Substituted quinolinones having herbicidal action

ABSTRACT

Substituted quinolinones of the formula I 
                         
in which the variables are defined according to the description, their agriculturally suitable salts, processes and intermediates for preparing the compounds of the formula I, compositions comprising them and their use as herbicides, i.e. for controlling harmful plants, and also a method for controlling unwanted vegetation which comprises allowing a herbicidally effective amount of at least one compound of the formula I to act on plants, their seed and/or their habitat.

This application claims priority under 35 U.S.C. §119 to European PatentApplication No. 09174833.5, filed Nov. 3, 2009, the entire contents ofwhich is hereby incorporated herein by reference.

The present invention relates to quinolinones of the formula I

in which the variables have the following meaning:

-   R¹ is O—R^(A), S(O)_(n)—R^(A) or O—S(O)_(n)—R^(A);    -   R^(A) is hydrogen, C₁-C₄-alkyl, Z—C₃-C₆-cycloalkyl,        C₁-C₄-haloalkyl, C₂-C₆-alkenyl, Z—C₃-C₆-cycloalkenyl,        C₂-C₆-alkynyl, Z-(tri-C₁-C₄-alkyl)silyl, Z—C(═O)—R^(a),        —NR^(i)—C(O)—NR^(i)R^(ii), Z—P(═O)(R^(a))₂, NR^(i)R^(ii), a 3-        to 7-membered monocyclic or 9- or 10-membered bicyclic        saturated, unsaturated or aromatic heterocycle which contains 1,        2, 3 or 4 heteroatoms selected from the group consisting of O, N        and S, which may be partially or fully substituted by groups        R^(a) and/or R^(b),        -   R^(a) is hydrogen, OH, C₁-C₈-alkyl, C₁-C₄-haloalkyl,            Z—C₃-C₆-cycloalkyl, C₂-C₈-alkenyl, Z—C₅-C₆-cycloalkenyl,            C₂-C₈-alkynyl, Z—C₁-C₆-alkoxy, Z—C₁-C₄-haloalkoxy,            Z—C₃-C₈-alkenyloxy, Z—C₃-C₈-alkynyloxy, NR^(i)R^(ii),            C₁-C₆-alkylsulfonyl, Z-(tri-C₁-C₄-alkyl)silyl, Z-phenyl,            Z-phenoxy, Z-phenylamino or a 5- or 6-membered monocyclic or            9- or 10-membered bicyclic heterocycle which contains 1, 2,            3 or 4 heteroatoms selected from the group consisting of O,            N and S, where the cyclic groups are unsubstituted or            substituted by 1, 2, 3, 4 or 5 groups R^(b);            -   R^(i), R^(ii) independently of one another are hydrogen,                C₁-C₈-alkyl, C₁-C₄-haloalkyl, C₃-C₈-alkenyl,                C₃-C₈-alkynyl, Z—C₃-C₆-cycloalkyl, Z—C₁-C₈-alkoxy,                Z—C₁-C₈-haloalkoxy, Z—C(═O)—R^(a), Z-phenyl, a 3- to                7-membered monocyclic or 9- or 10-membered bicyclic                saturated, unsaturated or aromatic heterocycle which                contains 1, 2, 3 or 4 heteroatoms selected from the                group consisting of O, N and S and which is attached via                Z;            -   R^(i) and R^(ii) together with the nitrogen atom to                which they are attached may also form a 5- or 6-membered                monocyclic or 9- or 10-membered bicyclic heterocycle                which contains 1, 2, 3 or 4 heteroatoms selected from                the group consisting of O, N and S;        -   Z is a covalent bond or C₁-C₄-alkylene;    -   n is 0, 1 or 2;-   R² is phenyl, naphthyl or a 5- or 6-membered monocyclic or 9- or    10-membered bicyclic aromatic heterocycle which contains 1, 2, 3 or    4 heteroatoms selected from the group consisting of O, N and S,    where the cyclic groups are unsubstituted or substituted by 1, 2, 3    or 4 groups R^(b);    -   R^(b) independently of one another are Z—CN, Z—OH, Z—NO₂,        Z-halogen, C₁-C₈-alkyl, C₁-C₄-haloalkyl, C₂-C₈-alkenyl,        C₂-C₈-alkynyl, Z—C₁-C₈-alkoxy, Z—C₁-C₈-haloalkoxy,        Z—C₃-C₁₀-cycloalkyl, O—Z—C₃-C₁₀-cycloalkyl, Z—C(═O)—R^(a),        NR^(i)R^(ii), Z-(tri-C₁-C₄-alkyl)silyl, Z-phenyl and        S(O)_(n)R^(bb),        -   where R^(bb) is C₁-C₈-alkyl or C₁-C₆-haloalkyl and        -   n is 0, 1 or 2;        -   R^(b) together with the group R^(b) attached to the adjacent            carbon atom may also form a five- or six-membered saturated            or partially or fully unsaturated ring which, in addition to            carbon atoms, may contain 1, 2 or 3 heteroatoms selected            from the group consisting of O, N and S;-   X is O, S or N—R⁵;    -   R³, R⁴, R⁵ independently of one another are hydrogen,        C₁-C₆-alkyl, C₁-C₄-haloalkyl, C₂-C₆-alkenyl, C₃-C₆-alkynyl,        Z—C₃-C₁₀-cycloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-cyanoalkyl,        Z-phenyl, Z—C(═O)—R^(a2) or tri-C₁-C₄-alkylsilyl;        -   R^(a2) is C₁-C₆-alkyl, C₁-C₄-haloalkyl, Z—C₁-C₆-alkoxy,            Z—C₁-C₄-haloalkoxy or NR^(i)R^(ii);-   A, E, G, M are N or C—R^(b), at least one of these groups being N;    -   R^(b) is hydrogen or one of the groups mentioned for R^(b);        where in the groups R^(A), R³, R⁴ and R⁵ and their substituents,        the carbon chains and/or the cyclic groups may be partially or        fully substituted by groups R^(b),        or a N-oxide or an agriculturally suitable salt thereof.

Moreover, the invention relates to processes and intermediates forpreparing the quinolinones of the formula I and the N-oxides thereof,the agriculturally usable salts thereof, and also to active compoundcombinations comprising them, to compositions comprising them and totheir use as herbicides, i.e. for controlling harmful plants, and alsoto a method for controlling unwanted vegetation which comprises allowinga herbicidally effective amount of at least one quinolinone of theformula I or of an agriculturally suitable salt of I to act on plants,their seed and/or their habitat.

Further embodiments of the present invention can be found in the claims,the description and the examples. It is to be understood that thefeatures mentioned above and those still to be illustrated below of thesubject matter of the invention can be applied not only in therespective given combination but also in other combinations withoutleaving the scope of the invention.

WO 2008/009908 and WO 2008/071918 describe herbicidal pyridopyrazines;however, their herbicidal action at low application rates and/or theircompatibility with crop plants leave scope for improvement.

It is an object of the present invention to provide compounds havingherbicidal action. To be provided are in particular active compoundshaving strong herbicidal action, in particular even at low applicationrates, whose compatibility with crop plants is sufficient for commercialapplication.

These and further objects are achieved by the compounds of the formula Idefined at the outset and by their N-oxides and also theiragriculturally suitable salts.

The quinolinones of the formula I according to the invention can beobtained analogously to known synthesis routes.

The reaction of the compounds of the formula II with hydroxylamine isusually carried out at temperatures of from −78° C. to 120° C.,preferably from 0° C. to 50° C., in an inert organic solvent in thepresence of a base [cf. lit. J. Med. Chem. 2008, 51, 392].

Suitable solvents are aliphatic hydrocarbons, aromatic hydrocarbons,such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, ethers,nitriles, ketones, and also dimethyl sulfoxide, dimethylformamide anddimethylacetamide, particularly preferably toluene. It is also possibleto use mixtures of the solvents mentioned.

Suitable bases are, in general, inorganic compounds, such as alkalimetal and alkaline earth metal hydroxides, alkali metal and alkalineearth metal oxides, alkali metal and alkaline earth metal hydrides,alkali metal amides, alkali metal and alkaline earth metal carbonates,and also alkali metal bicarbonates, organometallic compounds,alkylmagnesium halides, and also alkali metal and alkaline earth metalalkoxides, and dimethoxymagnesium, moreover organic bases, for exampletertiary amines, such as trimethylamine, triethylamine, tributylamine,diisopropylethylamine and N-methylpiperidine, pyridine, substitutedpyridines, such as collidine, lutidine and 4-dimethylaminopyridine, andalso bicyclic amines. Particular preference is given to pyridine.

The bases are generally employed in catalytic amounts; however, they canalso be used in equimolar amounts, in excess or, if appropriate, assolvents.

The starting materials of the formula II required for preparing thecompounds I are known from the literature [J. Org. Chem., 1984, 49 (12),2208] or can be prepared in accordance with the literature cited.

The reaction of the compounds of the formula III with formaldehyde ispreferably carried out with an aqueous formaldehyde solution usually attemperatures of from −78° C. to 120° C., preferably from 0° C. to 50°C., in an inert organic solvent in the presence of an acid [cf. lit. J.Org. Chem. 2001, 66, 7666].

Suitable solvents are water, aliphatic hydrocarbons, aromatichydrocarbons, halogenated hydrocarbons, ethers, nitriles, and alsodimethyl sulfoxide, dimethylformamide and dimethylacetamide,particularly preferably water. It is also possible to use mixtures ofthe solvents mentioned.

Suitable acids and acid catalysts are inorganic acids, such ashydrofluoric acid, hydrochloric acid, hydrobromic acid, sulfuric acidand perchloric acid, Lewis acids, such as boron trifluoride, aluminumtrichloride, iron(III) chloride, tin(IV) chloride, titanium(IV) chlorideand zinc(II) chloride, and also organic acids, such as formic acid,acetic acid, propionic acid, oxalic acid, toluenesulfonic acid,benzenesulfonic acid, camphorsulfonic acid, citric acid andtrifluoroacetic acid.

The acids are generally employed in catalytic amounts; however, they canalso be used in equimolar amounts, in excess or, if appropriate, assolvents.

The reaction of the compounds of the formula IV with diazomethanecompounds of the formula V is usually carried out at temperatures offrom −78° C. to 120° C., preferably from 0° C. to 50° C., in an inertorganic solvent [cf. Lit. Chem. Ber. 1969, 102, 2429].

Suitable solvents are aliphatic hydrocarbons, aromatic hydrocarbons,halogenated hydrocarbons, ethers, such as diethyl ether, diisopropylether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran,nitriles, ketones, and also dimethyl sulfoxide, dimethylformamide anddimethylacetamide, particularly preferably ethers. It is also possibleto use mixtures of the solvents mentioned.

The starting materials are generally reacted with one another inequimolar amounts.

The reaction mixtures are worked up in a customary manner, for exampleby mixing with water, separating the phases and, if appropriate,chromatographic purification of the crude products. Some of theintermediates and end products are obtained in the form of colorless orslightly brownish viscous oils which are purified or freed from volatilecomponents under reduced pressure and at moderately elevatedtemperature. If the intermediates and end products are obtained assolids, the purification can also be carried out by recrystallization ordigestion.

If the synthesis yields mixtures of isomers, a separation is generallyhowever not necessarily required since in some cases the individualisomers can be interconverted during work-up for use or duringapplication (for example under the action of light, acids or bases).Such conversions may also take place after application, for example inthe case of the treatment of plants in the treated plant or in theharmful plant to be controlled.

The organic moieties mentioned for the substituents of the compoundsaccording to the invention are collective terms for individualenumerations of the individual group members. All hydrocarbon chains,such as alkyl, haloalkyl, alkenyl, alkynyl, and the alkyl moieties andalkenyl moieties in alkoxy, haloalkoxy, alkylamino, dialkylamino,N-alkylsulfonylamino, alkenyloxy, alkynyloxy, alkoxyamino,alkylaminosulfonylamino, dialkylaminosulfonylamino, alkenylamino,alkynylamino, N-(alkenyl)-N-(alkyl)amino, N-(alkynyl)-N-(alkyl)amino,N-(alkoxy)-N-(alkyl)amino, N-(alkenyl)-N-(alkoxy)amino orN-(alkynyl)-N-(alkoxy)amino can be straight-chain or branched.

The prefix C_(n)-C_(m)— indicates the respective number of carbons ofthe hydrocarbon unit. Unless indicated otherwise, halogenatedsubstituents preferably carry one to five identical or different halogenatoms, in particular fluorine atoms or chlorine atoms.

The meaning halogen denotes in each case fluorine, chlorine, bromine oriodine.

Examples of other meanings are:

alkyl and the alkyl moieties for example in alkoxy, alkylamino,dialkylamino, N-alkylsulfonylamino, alkylaminosulfonylamino,dialkylaminosulfonylamino, N-(alkenyl)-N-(alkyl)amino,N-(alkynyl)-N-(alkyl)amino, N-(alkoxy)-N-(alkyl)amino: saturatedstraight-chain or branched hydrocarbon radicals having one or morecarbon atoms, for example 1 or 2, 1 to 4 or 1 to 6 carbon atoms, forexample C₁-C₆-alkyl, such as methyl, ethyl, propyl, 1-methylethyl,butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl,1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl,1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl,1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl,1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl. In one embodimentaccording to the invention, alkyl denotes small alkyl groups, such asC₁-C₄-alkyl. In another embodiment according to the invention, alkyldenotes relatively large alkyl groups, such as C₅-C₆-alkyl.

Haloalkyl: an alkyl radical as mentioned above, some or all of whosehydrogen atoms are substituted by halogen atoms, such as fluorine,chlorine, bromine and/or iodine, for example chloromethyl,dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl,trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl,chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl,2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl,2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl,2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl,3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl,2,2,3,3,3-pentafluoropropyl, heptafluoropropyl,1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl,1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyland nonafluorobutyl.

Cycloalkyl and the cycloalkyl moieties for example in cycloalkoxy orcycloalkylcarbonyl: monocyclic saturated hydrocarbon groups having threeor more carbon atoms, for example 3 to 6 carbon ring members, such ascyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

Alkenyl and the alkenyl moieties for example in alkenylamino,alkenyloxy, N-(alkenyl)-N-(alkyl)amino, N-(alkenyl)-N-(alkoxy)amino:monounsaturated straight-chain or branched hydrocarbon radicals havingtwo or more carbon atoms, for example 2 to 4, 2 to 6 or 3 to 6 carbonatoms, and a double bond in any position, for example C₂-C₆-alkenyl,such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl,2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl,1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl,3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl,3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl,3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl,3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl,1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl,1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl,1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl,4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl,3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl,2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl,1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl,4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl,1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl,2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,1-ethyl-2-methyl-1-propenyl, 1-ethyl-2-methyl-2-propenyl.

Cycloalkenyl: monocyclic monounsaturated hydrocarbon groups having 3 to6, preferably 5 or 6, carbon ring members, such as cyclopenten-1-yl,cyclopenten-3-yl, cyclohexen-1-yl, cyclohexen-3-yl, cyclohexen-4-yl.

Alkynyl and the alkynyl moieties for example in alkynyloxy,alkynylamino, N-(alkynyl)-N-(alkyl)amino or N-(alkynyl)-N-(alkoxy)amino:straight-chain or branched hydrocarbon groups having two or more carbonatoms, for example 2 to 4, 2 to 6 or 3 to 6 carbon atoms, and a triplebond in any position, for example C₂-C₆-alkynyl, such as ethynyl,1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl,1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl,1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl,3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl,1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl,1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl,2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl,3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl,1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl,2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl,1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl.

Alkoxy: alkyl as defined above which is attached via an oxygen atom, forexample methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy,1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy, pentoxy,1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy,1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy,1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy,1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy,2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy,1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy,1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or1-ethyl-2-methylpropoxy.

3- to 7-membered monocyclic or 9- or 10-membered bicyclic saturated,unsaturated or aromatic heterocycle which contains 1, 2, 3, or 4heteroatoms selected from the group consisting of O, N and S and whichcan be attached via C or N. Preferred from among these are 5- or6-membered heterocycles.

Saturated or unsaturated heterocyclic groups which are attached via N,such as: pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl,pyrimidin-5-yl, pyrazin-2-yl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl,pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, isoxazol-3-yl, isoxazol-4-yl,isoxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl,imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, oxazol-2-yl, oxazol-4-yl,oxazol-5-yl, thiazol-2-yl, thiazol-4-yl and thiazol-5-yl.

Heteroaromatic groups which are attached via C, such as: pyrazol-3-yl,imidazol-5-yl, oxazol-2-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl,pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrimidin-2-yl,pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-4-yl, pyrazin-2-yl,[1H]-tetrazol-5-yl and [2H]-tetrazol-5-yl.

The compounds of the formula I may, depending on the substitutionpattern, contain one or more further centers of chirality. Accordingly,the compounds according to the invention can be present as pureenantiomers or diastereomers or as enantiomer or diastereomer mixtures.The invention provides both the pure enantiomers or diastereomers andtheir mixtures.

The compounds of the formula I may also be present in the form of theN-oxides and/or of their agriculturally useful salts, the type of saltgenerally not being important. Suitable salts are generally the salts ofthose cations or the acid addition salts of those acids whose cationsand anions, respectively, have no adverse effect on the herbicidalactivity of the compounds I.

Suitable cations are in particular ions of the alkali metals, preferablylithium, sodium or potassium, of the alkaline earth metals, preferablycalcium or magnesium, and of the transition metals, preferablymanganese, copper, zinc or iron. Another cation that may be used isammonium, where, if desired, one to four hydrogen atoms may be replacedby C₁-C₄-alkyl, hydroxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or benzyl, preferably ammonium,dimethylammonium, diisopropylammonium, tetramethylammonium,tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium,di(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium. Another suitableammonium cation is the pyridine nitrogen atom of the formula Iquaternized by alkylation or arylation. Also suitable are phosphoniumions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium, orsulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

Anions of suitable acid addition salts are primarily chloride, bromide,fluoride, hydrogensulfate, sulfate, dihydrogenphosphate,hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate,hexafluorophosphate, benzoate and also the anions of C₁-C₄-alkanoicacids, preferably formate, acetate, propionate, butyrate ortrifluoroacetate.

With respect to the variables, the particularly preferred embodiments ofthe intermediates correspond to those of the groups of the formula I.

In a particular embodiment, the variables of the compounds of theformula I have the following meanings, these meanings, both on their ownand in combination with one another, being particular embodiments of thecompounds of the formula I:

In one preferred embodiment of the compounds of the formula I, A is Nand E, G and M are C—R^(c). These compounds correspond to the formulaI.1

in which the groups R³ and R⁴ are hydrogen and R^(c1), R^(c2) and R^(c3)each correspond to a group R^(c) and preferably have the followingmeanings:

R^(c1) is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H;

R^(c2) is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H,Br, OH and OCH₃;

R^(c3) is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H.

In a further embodiment of the compounds of the formula I, A, E and Mare C—R^(c) and G is N. These compounds correspond to the formula I.2

in which the groups R³ and R⁴ are hydrogen and R^(c1), R^(c2) and R^(c4)each correspond to a group R^(c) and preferably have the followingmeanings:

R^(c1) is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H;

R^(c2) is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H;and

R^(c3) is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H,Br, OH and OCH₃.

In a further embodiment of the compounds of the formula I, A and G are Nand E and M are C—R^(c). These compounds correspond to the formula I.3

in which the groups R³ and R⁴ are hydrogen and R^(c1) and R^(c3) eachcorrespond to a group R^(c) and preferably have the following meanings:

R^(c1) is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H,Br, OH and OCH₃;

R^(c2) is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H,Br, OH and OCH₃.

In a further embodiment of the compounds of the formula I, A and M are Nand E and G are C—R^(c). These compounds correspond to the formula I.4

in which the groups R³ and R⁴ are hydrogen and R^(c2) and R^(c3) eachcorrespond to a group R^(c) and preferably have the following meanings:

R^(c2) is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H;

R^(c1) is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H,Br, OH and OCH₃.

In a further embodiment of the compounds of the formula I, A and E are Nand G and M are C—R^(c). These compounds correspond to the formula I.5,

in which the groups R³ and R⁴ are hydrogen and R^(c3) and R^(c4) eachcorrespond to a group R^(c) and preferably have the following meanings:

R^(c1) is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H,Br, OH and OCH₃;

R^(c2) is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H.

Particularly preferred aspects of the compounds of the formula I relateto those of each of the formulae I.1 to I.5 in which the variables havethe meanings preferred for formula I.

In a first preferred embodiment of the invention, R¹ is O—R^(A).

In a further preferred embodiment of the invention, R¹ is S(O)_(n)—R^(A)where n is preferably 0 or 2, in particular 2.

In a further preferred embodiment, R¹ is O—S(O)_(n)—R^(A), where n ispreferably 0 or 2, in particular 2, such as, for example, OS(O)₂—CH₃,OS(O)₂—O₂H₅, OS(O)₂—C₃H₇, OS(O)₂—C₆H₅ or OS(O)₂-(4-CH₃—C₆H₄).

In a further preferred embodiment, R¹ is O—S(O), —NR^(i)R^(ii), whichhas in particular the groups NR^(i)R^(ii) mentioned below as beingpreferred.

R^(A) is in particular H, C₁-C₆-alkylcarbonyl, such as C(O)CH₃,C(O)CH₂CH₃, C(O)CH(CH₃)₂ or C(O)C(CH₃)₃; C₁-C₆-cycloalkylcarbonyl, suchas cyclopropylcarbonyl, cyclopentylcarbonyl or cyclohexylcarbonyl;C₂-C₆-alkenylcarbonyl, such as C(O)CH═CH₂ or C(O)CH₂CH═CH₂, optionallysubst. benzoyl, such as C(O)C₆H₅, C(O)[2-CH₃—C₆H₄], C(O)[4-CH₃—C₆H₄],C(O)[2-F—C₆H₄], C(O)[4-F—C₆H₄], or optionally subst. heteroaryl, such aspyridine, which is attached via a carbonyl group. Particularlypreferably, R^(A) is H or C₁-C₆-alkylcarbonyl.

More particularly preferably, R^(A) is selected from the groupconsisting of H, OCH₃, C(O)CH₃, C(O)CH₂CH₃, C(O)CH(CH₃)₂, C(O)C(CH₃)₃,C(O)-c-C₃H₅, C(O)—C₆H₅, C(O)—CH₂C₆H₅, C(O)CH₂Cl, C(O)CF₃, C(O)CH₂OCH₃,C(O)N(CH₃)₂ and C(O)OCH₂CH₃.

In a further preferred embodiment of the invention, R^(A) isNR^(i)R^(ii).

In a further preferred embodiment of the invention, R^(A) isZ—NR^(i)—C(O)—NR^(i)R^(ii), where R^(i) and R^(ii) are as defined at theoutset and preferably as defined below. In further embodiments,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy and C₁-C₄-alkoxy-C₁-C₄-alkyl, inparticular OCH₃, OC₂H₅, CH₂CH₂OCH₃ and CH₂CH₂Cl, may also be possiblefor R^(i) and R^(ii), independently of one another.

R^(i) and R^(ii) are preferably C₁-C₈-alkyl, C₁-C₄-haloalkyl,Z—C₃-C₆-cycloalkyl, Z—C₁-C₈-alkoxy, Z—C₁-C₈-haloalkoxy, Z-phenyl,Z—C(═O)—R^(a) or Z-hetaryl. Here, preference is given to CH₃, C₂H₅,n-propyl, CH(CH₃)₂, butyl, 2-chloroethyl, cyclopentyl, cyclohexyl,2-ethoxymethyl, 2-chloroethoxy, phenyl, pyrimidines or triazines whoserings are unsubstituted or substituted. Here, preferred substituents areC₁-C₄-alkylcarbonyl or C₁-C₄-haloalkylcarbonyl, in particular C(═O)—CH₃,C(═O)—C₂H₅, C(═O)—C₃H₇, C(═O)—CH(CH₃)₂, butylcarbonyl and C(═O)—CH₂Cl.Particularly preferred aspects of the group NR^(i)R^(ii) areN(di-C₁-C₄-alkyl), in particular N(CH₃)—C₁-C₄-alkyl, such as N(CH₃)₂,N(CH₃)CH₂CH₃, N(CH₃)C₃H₇ and N(CH₃)CH(CH₃)₂.

Further particularly preferred aspects of NR^(i)R^(ii) are NH-aryl,where aryl is preferably phenyl which is substituted—in particular inthe 2- and 6-position—by one to three identical or different halogen,CH₃, halo-C₁-C₂-alkyl, halo-C₁-C₂-alkoxy and carboxyl groups, such as2-C₁₋₆—COOH—C₆H₃, 2,6-Cl₂-C₆H₃, 2,6-Cl₂-C₆H₃, 2,6-Cl₂-3-C₆H₂, 2-CF₃,6-CH₂CHF₂—C₆H₃, 2-CF₃-6-OCF₃—C₆H₃ and 2-CF₃-6-CH₂CHF₂—C₆H₃.

Further aspects of NR^(i)R^(ii) are NH-heteroaryl, where heteroaryl ispreferably one of the preferred heteroaromatic groups below, inparticular triazinyl, pyrimidinyl or triazolopyrimidinyl, such as[1,2,4]triazolo[1,5-a]pyrimidin-2-yl, which groups may be substituted,in particular by C₁-C₄-alkoxy and/or halogen. Particular preference isgiven to 5,7-dimethoxy-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl,5,7-diethoxy-[1,2,4]-triazolo[1,5-a]pyrimidin-2-yl,5-fluoro-7-methoxy-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl and5-fluoro-7-ethoxy-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl.

In particularly preferred embodiments of the compounds of the formula Iand in particular those of the formula I.1, R¹ is selected from thegroup consisting of OH, OCH₃, OC(O)CH₃, OC(O)CH₂CH₃, OC(O)CH(CH₃)₂,OC(O)C(CH₃)₃, OC(O)-c-C₃H₅, OC(O)—C₆H₅, OC(O)—CH₂C₆H₅, OC(O)CH₂Cl,OC(O)—CF₃, OC(O)—CH₂OCH₃, OC(O)—N(CH₃)₂ and OC(O)—OCH₂CH₃.

In particularly preferred embodiments of the compounds of the formula Iand in particular those of the formula I.1, R² is phenyl which issubstituted by a group selected from the group consisting of 2-Br, 2-Cl,2,4-Cl₂, 2-Cl-4-F, 2-Cl-5-F, 2-Cl-6-F, 2-Cl-4-CF₃, 2-Cl-5-CF₃,2-Cl-6-CF₃, 2-Cl-3,6-F₂, 2-F, 2,4-F₂, 2,5-F₂, 2,6-F₂, 2-F-4-CF₃,2-F-5-CF₃, 2-F-6-CF₃, 2,3,6-F₃, 2-NO₂, 2-NO₂-4-F, 2-NO₂-5-F, 2-NO₂-6-F,2-NO₂-4-CF₃, 2-NO₂-5-CF₃, 2-NO₂-6-CF₃, 2-NO₂-3,6-F₂, 2-CN, 2-CH₃,2-CH₃-4-F, 2-CH₃-5-F, 2-CH₃-6-F, 2-CH₃-4-CF₃, 2-CH₃-5-CF₃, 2-CH₃-6-CF₃,2-CH₃-3,6-F₂, 2-OCH₃, 2-OCH₃-4-F, 2-OCH₃-5-F, 2-OCH₃-6-F, 2-OCH₃-4-CF₃,2-OCH₃-5-CF₃, 2-OCH₃-6-CF₃, 2-OCH₃-3,6-F₂, 2-CH F₂, 2-CHF₂-4-F,2-CHF₂-5-F, 2-CHF₂-6-F, 2-CHF₂-4-CF₃, 2-CHF₂-5-CF₃, 2-CH F₂-6-CF₃,2-CHF₂-3,6-F₂, 2-CF₃, 2-CF₃-4-F, 2-CF₃-5-F, 2-CF₃-6-F, 2-CF₃-4-CF₃,2-CF₃-5-CF₃, 2-CF₃-6-CF₃, 2-CF₃-3,6-F₂, 2-OCHF₂, 2-OCHF₂-4-F,2-OCHF₂-5-F, 2-OCHF₂-6-F, 2-OCHF₂-4-CF₃, 2-OCHF₂-5-CF₃, 2-OCHF₂-6-CF₃,2-OCHF₂-3,6-F₂, 2-OCF₃, 2-OCF₃-4-F, 2-OCF₃-5-F, 2-OCF₃-6-F,2-OCF₃-4-CF₃, 2-OCF₃-5-CF₃, 2-OCF₃-6-CF₃ and 2-OCF₃-3,6-F₂.

In a further preferred embodiment of the invention, R^(A) is a 5- or6-membered heterocycle optionally substituted by R^(b) as defined above,which preferably has either 1, 2, 3 or 4 nitrogen atoms or 1 oxygen or 1sulfur atom and if appropriate 1 or 2 nitrogen atoms as ring members andwhich is unsubstituted or may have 1 or 2 substituents selected fromR^(b). Preference is given to saturated or unsaturated groups attachedvia nitrogen, such as, for example:

Heteroaromatic groups: pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl,pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl, 2-furyl, 3-furyl,2-thienyl, 3-thienyl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl,isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, isothiazol-3-yl,isothiazol-4-yl, isothiazol-5-yl, imidazol-1-yl, imidazol-2-yl,imidazol-4-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl,thiazol-4-yl and thiazol-5-yl;

In another aspect, R^(A) is a heteroaromatic group attached via carbon,such as pyrazol-3-yl, imidazol-5-yl, oxazol-2-yl, thiazol-2-yl,thiazol-4-yl, thiazol-5-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl,pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-4-yl,pyrazin-2-yl, [1H]-tetrazol-5-yl and [2H]-tetrazol-5-yl, where each ofthe heterocycles mentioned here in an exemplary manner may have 1 or 2substituents selected from R^(b). Preferred groups R^(b) are inparticular F, Cl, CN, NO₂, CH₃, C₂H₅, OCH₃, OC₂H₅, OCHF₂, OCF₃ and CF₃.

In a further preferred aspect, R² is phenyl which is unsubstituted orpartially or fully substituted by groups R^(b). Particular preference isgiven to compounds in which a group R^(b) is located in theortho-position. Such compounds of the formula I are described by theformula I.A:

In formula I.A, the index m is zero or an integer from one to four,preferably 0, 1 or 2, in particular 0 or 1. R⁶ and R⁷ are groups R^(b)as defined at the outset, preferably halogen, NO₂, C₁-C₄-alkyl,C₁-C₂-haloalkyl and C₁-C₄-alkoxy. One group R⁷ is preferably located inposition 5. A group R⁷ in position 3 is a further preferred embodiment.

Particularly preferably, R⁶ is Br, F, NO₂, CN, CH₃, OCH₃, CF₃, OCF₃,CHF₂ or OCHF₂. R⁶ is particularly preferably halogen or halomethyl, suchas Cl, F or CF₃. Especially preferably, (R⁷)_(m) is selected from thegroup consisting of 4-F, 5-F, 6-F, 4-CF₃, 5-CF₃ and 3,6-F₂.

The groups R³ and R⁴ are preferably hydrogen.

In a preferred embodiment, X is O.

In a further embodiment, X is S.

In a further embodiment, X is NR⁵.

R⁵ is preferably H, C₁-C₆-alkyl, such as CH₃, C₂H₅, n-C₃H₇, CH(CH₃)₂,n-C₃H₉, or C(CH₃)₃; C₃-C₆-cycloalkyl-C₁-C₄-alkyl, such ascyclopropylmethyl, C₃-C₆-alkenyl, such as CH₂CH═CH₂, CH₂C(CH₃)═CH₂,CH₂CH₂H═CH₂, CH₂CH₂C(CH₃)—CH₂, CH₂CH₂CH₂CH═CH₂, CH₂CH₂CH₂C(CH₃)═CH₂, oroptionally subst. phenyl, such as C₆H₅, 4-CH₃—C₆H₄, 4-F—C₆H₄ orS(O)_(n)—R^(N), where R^(N) is C₁-C₆-haloalkyl, such as CH₂CF₃, CH₂CHF₂.

A further embodiment relates to the N-oxides of the compounds of theformula I.

A further embodiment relates to salts of the compounds of the formula I,in particular those which are obtainable by quaternization of thepyridine nitrogen atom, which may preferably take place by alkylation orarylation of the compounds of the formula I. Preferred salts of thecompounds are thus the N-alkyl salts, in particular the N-methyl salts,and the N-phenyl salts.

In particular with a view to their use, preference is given to thecompounds of the formula I compiled in the tables below, which compoundscorrespond to the formulae I.1A*, I.2A*, I.3A*, I.4A* and I.5A*,respectively. The groups mentioned for a substituent in the tables arefurthermore per se, independently of the combination in which they arementioned, a particularly preferred aspect of the substituent inquestion.

Table 1

Compounds of the formula I.1A*, in which X is oxygen, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 2

Compounds of the formula I.1A*, in which X is oxygen, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 3

Compounds of the formula I.1A*, in which X is oxygen, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 4

Compounds of the formula I.1A*, in which X is oxygen, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 5

Compounds of the formula I.1A*, in which X is oxygen, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 6

Compounds of the formula I.1A*, in which X is oxygen, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 7

Compounds of the formula I.1A*, in which X is oxygen, (R⁷)_(m) is 4-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 8

Compounds of the formula I.1A*, in which X is oxygen, (R⁷)_(m) is 5-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 9

Compounds of the formula I.1A*, in which X is oxygen, (R⁷)_(m) is 3,6-F₂and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 10

Compounds of the formula I.1A*, in which X is sulfur, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 11

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 12

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 13

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 14

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 15

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 16

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_(m) is 4-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 17

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_(m) is 5-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 18

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_(m) is 3,6-F₂and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 19

Compounds of the formula I.1A*, in which X is sulfur, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 20

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 21

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 22

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 23

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 24

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 25

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_(m) is 4-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 26

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_(m) is 5-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 27

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_(m) is 3,6-F₂and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 28

Compounds of the formula I.1A*, in which X is N—H, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 29

Compounds of the formula I.1A*, in which X is N—CH₃, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 30

Compounds of the formula I.1A*, in which X is N—C₂H₅, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 31

Compounds of the formula I.1A*, in which X is N-n-C₃H₇, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 32

Compounds of the formula I.1A*, in which X is N—CH(CH₃)₂, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 33

Compounds of the formula I.1A*, in which X is N-n-C₄H₉, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 34

Compounds of the formula I.1A*, in which X is N—CH₂CH═CH₂, the index min (R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 35

Compounds of the formula I.1A*, in which X is N—CH₂C≡CH, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 36

Compounds of the formula I.1A*, in which X is N—CH₂CN, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 37

Compounds of the formula I.1A*, in which X is N—CH₂CF₃, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 38

Compounds of the formula I.1A*, in which X is N—CH₂C₆H₅, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 39

Compounds of the formula I.1A*, in which X is N—H, (R⁷)_(m) is 4-Cl andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 40

Compounds of the formula I.1A*, in which X is N—CH₃, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 41

Compounds of the formula I.1A*, in which X is N—C₂H₅, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 42

Compounds of the formula I.1A*, in which X is N-n-C₃H₇, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 43

Compounds of the formula I.1A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is4-Cl and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 44

Compounds of the formula I.1A*, in which X is N-n-C₄H₉, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 45

Compounds of the formula I.1A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is4-Cl and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 46

Compounds of the formula I.1A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is4-Cl and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 47

Compounds of the formula I.1A*, in which X is N—CH₂CN, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 48

Compounds of the formula I.1A*, in which X is N—CH₂CF₃, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 49

Compounds of the formula I.1A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is4-Cl and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 50

Compounds of the formula I.1A*, in which X is N—H, (R⁷)_(m) is 3-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 51

Compounds of the formula I.1A*, in which X is N—CH₃, (R⁷)_(m) is 3-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 52

Compounds of the formula I.1A*, in which X is N—C₂H₅, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 53

Compounds of the formula I.1A*, in which X is N-n-C₃H₇, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 54

Compounds of the formula I.1A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is3-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 55

Compounds of the formula I.1A*, in which X is N-n-C₄H₉, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 56

Compounds of the formula I.1A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is3-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 57

Compounds of the formula I.1A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 58

Compounds of the formula I.1A*, in which X is N—CH₂CN, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 59

Compounds of the formula I.1A*, in which X is N—CH₂CF₃, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 60

Compounds of the formula I.1A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 61

Compounds of the formula I.1A*, in which X is N—H, (R⁷)_(m) is 4-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 62

Compounds of the formula I.1A*, in which X is N—CH₃, (R⁷)_(m) is 4-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 63

Compounds of the formula I.1A*, in which X is N—C₂H₅, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 64

Compounds of the formula I.1A*, in which X is N-n-C₃H₇, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 65

Compounds of the formula I.1A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is4-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 66

Compounds of the formula I.1A*, in which X is N-n-C₄H₉, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 67

Compounds of the formula I.1A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is4-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 68

Compounds of the formula I.1A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 69

Compounds of the formula I.1A*, in which X is N—CH₂CN, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 70

Compounds of the formula I.1A*, in which X is N—CH₂CF₃, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 71

Compounds of the formula I.1A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 72

Compounds of the formula I.1A*, in which X is N—H, (R⁷)_(m) is 5-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 73

Compounds of the formula I.1A*, in which X is N—CH₃, (R⁷)_(m) is 5-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 74

Compounds of the formula I.1A*, in which X is N—C₂H₅, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 75

Compounds of the formula I.1A*, in which X is N-n-C₃H₇, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 76

Compounds of the formula I.1A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is5-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 77

Compounds of the formula I.1A*, in which X is N-n-C₄H₉, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 78

Compounds of the formula I.1A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is5-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 79

Compounds of the formula I.1A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 80

Compounds of the formula I.1A*, in which X is N—CH₂CN, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 81

Compounds of the formula I.1A*, in which X is N—CH₂CF₃, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 82

Compounds of the formula I.1A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 83

Compounds of the formula I.1A*, in which X is N—H, (R⁷)_(m) is 6-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 84

Compounds of the formula I.1A*, in which X is N—CH₃, (R⁷)_(m) is 6-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 85

Compounds of the formula I.1A*, in which X is N—C₂H₅, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 86

Compounds of the formula I.1A*, in which X is N-n-C₃H₇, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 87

Compounds of the formula I.1A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is6-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 88

Compounds of the formula I.1A*, in which X is N-n-C₄H₉, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 89

Compounds of the formula I.1A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is6-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 90

Compounds of the formula I.1A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 91

Compounds of the formula I.1A*, in which X is N—CH₂CN, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 92

Compounds of the formula I.1A*, in which X is N—CH₂CF₃, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 93

Compounds of the formula I.1A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 94

Compounds of the formula I.1A*, in which X is N—H, (R⁷)_(m) is 4-CF₃ andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 95

Compounds of the formula I.1A*, in which X is N—CH₃, (R⁷)_(m) is 4-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 96

Compounds of the formula I.1A*, in which X is N—C₂H₅, (R⁷)_(m) is 4-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 97

Compounds of the formula I.1A*, in which X is N-n-C₃H₇, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 98

Compounds of the formula I.1A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 99

Compounds of the formula I.1A*, in which X is N-n-C₄H₉, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 100

Compounds of the formula I.1A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 101

Compounds of the formula I.1A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 102

Compounds of the formula I.1A*, in which X is N—CH₂CN, (R⁷)_(m) is 4-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 103

Compounds of the formula I.1A*, in which X is N—CH₂CF₃, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 104

Compounds of the formula I.1A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 105

Compounds of the formula I.1A*, in which X is N—H, (R⁷)_(m) is 5-CF₃ andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 106

Compounds of the formula I.1A*, in which X is N—CH₃, (R⁷)_(m) is 5-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 107

Compounds of the formula I.1A*, in which X is N—C₂H₅, (R⁷)_(m) is 5-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 108

Compounds of the formula I.1A*, in which X is N-n-C₃H₇, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 109

Compounds of the formula I.1A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 110

Compounds of the formula I.1A*, in which X is N-n-C₄H₉, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 111

Compounds of the formula I.1A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 112

Compounds of the formula I.1A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 113

Compounds of the formula I.1A*, in which X is N—CH₂CN, (R⁷)_(m) is 5-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 114

Compounds of the formula I.1A*, in which X is N—CH₂CF₃, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 115

Compounds of the formula I.1A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 116

Compounds of the formula I.1A*, in which X is N—H, (R⁷)_(m) is 3,6-F₂and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 117

Compounds of the formula I.1A*, in which X is N—CH₃, (R⁷)_(m) is 3,6-F₂and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 118

Compounds of the formula I.1A*, in which X is N—C₂H₅, (R⁷)_(m) is 3,6-F₂and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 119

Compounds of the formula I.1A*, in which X is N-n-C₃H₇, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 120

Compounds of the formula I.1A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 121

Compounds of the formula I.1A*, in which X is N-n-C₄H₉, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 122

Compounds of the formula I.1A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 123

Compounds of the formula I.1A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 124

Compounds of the formula I.1A*, in which X is N—CH₂CN, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 125

Compounds of the formula I.1A*, in which X is N—CH₂CF₃, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 126

Compounds of the formula I.1A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 127

Compounds of the formula I.2A*, in which X is oxygen, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 128

Compounds of the formula I.2A*, in which X is oxygen, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 129

Compounds of the formula I.2A*, in which X is oxygen, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 130

Compounds of the formula I.2A*, in which X is oxygen, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 131

Compounds of the formula I.2A*, in which X is oxygen, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 132

Compounds of the formula I.2A*, in which X is oxygen, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 133

Compounds of the formula I.2A*, in which X is oxygen, (R⁷)_(m) is 4-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 134

Compounds of the formula I.2A*, in which X is oxygen, (R⁷)_(m) is 5-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 135

Compounds of the formula I.2A*, in which X is oxygen, (R⁷)_(m) is 3,6-F₂and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 136

Compounds of the formula I.2A*, in which X is sulfur, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 137

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 138

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 139

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 140

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 141

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 142

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_(m) is 4-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 143

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_(m) is 5-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 144

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_(m) is 3,6-F₂and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 145

Compounds of the formula I.2A*, in which X is sulfur, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 146

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 147

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 148

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 149

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 150

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 151

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_(m) is 4-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 152

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_(m) is 5-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 153

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_(m) is 3,6-F₂and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 154

Compounds of the formula I.2A*, in which X is N—H, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 155

Compounds of the formula I.2A*, in which X is N—CH₃, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 156

Compounds of the formula I.2A*, in which X is N—C₂H₅, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 157

Compounds of the formula I.2A*, in which X is N-n-C₃H₇, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 158

Compounds of the formula I.2A*, in which X is N—CH(CH₃)₂, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 159

Compounds of the formula I.2A*, in which X is N-n-C₄H₉, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 160

Compounds of the formula I.2A*, in which X is N—CH₂CH═CH₂, the index min (R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 161

Compounds of the formula I.2A*, in which X is N—CH₂C≡CH, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 162

Compounds of the formula I.2A*, in which X is N—CH₂CN, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 163

Compounds of the formula I.2A*, in which X is N—CH₂CF₃, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 164

Compounds of the formula I.2A*, in which X is N—CH₂C₆H₅, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 165

Compounds of the formula I.2A*, in which X is N—H, (R⁷)_(m) is 4-Cl andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 166

Compounds of the formula I.2A*, in which X is N—CH₃, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 167

Compounds of the formula I.2A*, in which X is N—C₂H₅, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 168

Compounds of the formula I.2A*, in which X is N-n-C₃H₇, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 169

Compounds of the formula I.2A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is4-Cl and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 170

Compounds of the formula I.2A*, in which X is N-n-C₄H₉, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 171

Compounds of the formula I.2A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is4-Cl and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 172

Compounds of the formula I.2A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is4-Cl and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 173

Compounds of the formula I.2A*, in which X is N—CH₂CN, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 174

Compounds of the formula I.2A*, in which X is N—CH₂CF₃, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 175

Compounds of the formula I.2A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is4-Cl and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 176

Compounds of the formula I.2A*, in which X is N—H, (R⁷)_(m) is 3-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 177

Compounds of the formula I.2A*, in which X is N—CH₃, (R⁷)_(m) is 3-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 178

Compounds of the formula I.2A*, in which X is N—C₂H₅, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 179

Compounds of the formula I.2A*, in which X is N-n-C₃H₇, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 180

Compounds of the formula I.2A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is3-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 181

Compounds of the formula I.2A*, in which X is N-n-C₄H₉, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 182

Compounds of the formula I.2A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is3-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 183

Compounds of the formula I.2A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 184

Compounds of the formula I.2A*, in which X is N—CH₂CN, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 185

Compounds of the formula I.2A*, in which X is N—CH₂CF₃, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 186

Compounds of the formula I.2A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 187

Compounds of the formula I.2A*, in which X is N—H, (R⁷)_(m) is 4-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 188

Compounds of the formula I.2A*, in which X is N—CH₃, (R⁷)_(m) is 4-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 189

Compounds of the formula I.2A*, in which X is N—C₂H₅, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 190

Compounds of the formula I.2A*, in which X is N-n-C₃H₇, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 191

Compounds of the formula I.2A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is4-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 192

Compounds of the formula I.2A*, in which X is N-n-C₄H₉, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 193

Compounds of the formula I.2A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is4-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 194

Compounds of the formula I.2A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 195

Compounds of the formula I.2A*, in which X is N—CH₂CN, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 196

Compounds of the formula I.2A*, in which X is N—CH₂CF₃, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 197

Compounds of the formula I.2A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 198

Compounds of the formula I.2A*, in which X is N—H, (R⁷)_(m) is 5-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 199

Compounds of the formula I.2A*, in which X is N—CH₃, (R⁷)_(m) is 5-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 200

Compounds of the formula I.2A*, in which X is N—C₂H₅, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 201

Compounds of the formula I.2A*, in which X is N-n-C₃H₇, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 202

Compounds of the formula I.2A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is5-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 203

Compounds of the formula I.2A*, in which X is N-n-C₄H₉, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 204

Compounds of the formula I.2A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is5-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 205

Compounds of the formula I.2A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 206

Compounds of the formula I.2A*, in which X is N—CH₂CN, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 207

Compounds of the formula I.2A*, in which X is N—CH₂CF₃, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 208

Compounds of the formula I.2A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 209

Compounds of the formula I.2A*, in which X is N—H, (R⁷)_(m) is 6-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 210

Compounds of the formula I.2A*, in which X is N—CH₃, (R⁷)_(m) is 6-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 211

Compounds of the formula I.2A*, in which X is N—C₂H₅, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 212

Compounds of the formula I.2A*, in which X is N-n-C₃H₇, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 213

Compounds of the formula I.2A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is6-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 214

Compounds of the formula I.2A*, in which X is N-n-C₄H₉, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 215

Compounds of the formula I.2A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is6-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 216

Compounds of the formula I.2A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 217

Compounds of the formula I.2A*, in which X is N—CH₂CN, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 218

Compounds of the formula I.2A*, in which X is N—CH₂CF₃, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 219

Compounds of the formula I.2A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 220

Compounds of the formula I.2A*, in which X is N—H, (R⁷)_(m) is 4-CF₃ andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 221

Compounds of the formula I.2A*, in which X is N—CH₃, (R⁷)_(m) is 4-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 222

Compounds of the formula I.2A*, in which X is N—C₂H₅, (R⁷)_(m) is 4-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 223

Compounds of the formula I.2A*, in which X is N-n-C₃H₇, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 224

Compounds of the formula I.2A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 225

Compounds of the formula I.2A*, in which X is N-n-C₄H₉, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 226

Compounds of the formula I.2A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 227

Compounds of the formula I.2A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 228

Compounds of the formula I.2A*, in which X is N—CH₂CN, (R⁷)_(m) is 4-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 229

Compounds of the formula I.2A*, in which X is N—CH₂CF₃, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 230

Compounds of the formula I.2A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 231

Compounds of the formula I.2A*, in which X is N—H, (R⁷)_(m) is 5-CF₃ andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 232

Compounds of the formula I.2A*, in which X is N—CH₃, (R⁷)_(m) is 5-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 233

Compounds of the formula I.2A*, in which X is N—C₂H₅, (R⁷)_(m) is 5-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 234

Compounds of the formula I.2A*, in which X is N-n-C₃H₇, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 235

Compounds of the formula I.2A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 236

Compounds of the formula I.2A*, in which X is N-n-C₄H₉, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 237

Compounds of the formula I.2A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 238

Compounds of the formula I.2A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 239

Compounds of the formula I.2A*, in which X is N—CH₂CN, (R⁷)_(m) is 5-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 240

Compounds of the formula I.2A*, in which X is N—CH₂CF₃, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 241

Compounds of the formula I.2A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 242

Compounds of the formula I.2A*, in which X is N—H, (R⁷)_(m) is 3,6-F₂and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 243

Compounds of the formula I.2A*, in which X is N—CH₃, (R⁷)_(m) is 3,6-F₂and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 244

Compounds of the formula I.2A*, in which X is N—C₂H₅, (R⁷)_(m) is 3,6-F₂and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 245

Compounds of the formula I.2A*, in which X is N-n-C₃H₇, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 246

Compounds of the formula I.2A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 247

Compounds of the formula I.2A*, in which X is N-n-C₄H₉, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 248

Compounds of the formula I.2A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 249

Compounds of the formula I.2A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 250

Compounds of the formula I.2A*, in which X is N—CH₂CN, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 251

Compounds of the formula I.2A*, in which X is N—CH₂CF₃, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 252

Compounds of the formula I.2A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 253

Compounds of the formula I.3A*, in which X is oxygen, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 254

Compounds of the formula I.3A*, in which X is oxygen, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 255

Compounds of the formula I.3A*, in which X is oxygen, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 256

Compounds of the formula I.3A*, in which X is oxygen, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 257

Compounds of the formula I.3A*, in which X is oxygen, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 258

Compounds of the formula I.3A*, in which X is oxygen, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 259

Compounds of the formula I.3A*, in which X is oxygen, (R⁷)_(m) is 4-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 260

Compounds of the formula I.3A*, in which X is oxygen, (R⁷)_(m) is 5-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 261

Compounds of the formula I.3A*, in which X is oxygen, (R⁷)_(m) is 3,6-F₂and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 262

Compounds of the formula I.3A*, in which X is sulfur, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 263

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 264

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 265

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 266

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 267

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_(m) is 6-Fand the combination of Wand R⁶ for a compound corresponds in each caseto one row of Table A

Table 268

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_(m) is 4-CF₃and the combination of Wand R⁶ for a compound corresponds in each caseto one row of Table A

Table 269

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_(m) is 5-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 270

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_(m) is 3,6-F₂and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 271

Compounds of the formula I.3A*, in which X is sulfur, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 272

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 273

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 274

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 275

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 276

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 277

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_(m) is 4-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 278

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_(m) is 5-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 279

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_(m) is 3,6-F₂and the combination of Wand R⁶ for a compound corresponds in each caseto one row of Table A

Table 280

Compounds of the formula I.3A*, in which X is N—H, the index m in(R⁷)_(m) is zero and the combination of Wand R⁶ for a compoundcorresponds in each case to one row of Table A

Table 281

Compounds of the formula I.3A*, in which X is N—CH₃, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 282

Compounds of the formula I.3A*, in which X is N—C₂H₅, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 283

Compounds of the formula I.3A*, in which X is N-n-C₃H₇, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 284

Compounds of the formula I.3A*, in which X is N—CH(CH₃)₂, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 285

Compounds of the formula I.3A*, in which X is N-n-C₄H₉, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 286

Compounds of the formula I.3A*, in which X is N—CH₂CH═CH₂, the index min (R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 287

Compounds of the formula I.3A*, in which X is N—CH₂C≡CH, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 288

Compounds of the formula I.3A*, in which X is N—CH₂CN, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 289

Compounds of the formula I.3A*, in which X is N—CH₂CF₃, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 290

Compounds of the formula I.3A*, in which X is N—CH₂C₆H₅, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 291

Compounds of the formula I.3A*, in which X is N—H, (R⁷)_(m) is 4-Cl andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 292

Compounds of the formula I.3A*, in which X is N—CH₃, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 293

Compounds of the formula I.3A*, in which X is N—C₂H₅, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 294

Compounds of the formula I.3A*, in which X is N-n-C₃H₇, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 295

Compounds of the formula I.3A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is4-Cl and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 296

Compounds of the formula I.3A*, in which X is N-n-C₄H₉, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 297

Compounds of the formula I.3A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is4-Cl and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 298

Compounds of the formula I.3A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is4-Cl and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 299

Compounds of the formula I.3A*, in which X is N—CH₂CN, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 300

Compounds of the formula I.3A*, in which X is N—CH₂CF₃, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 301

Compounds of the formula I.3A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is4-Cl and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 302

Compounds of the formula I.3A*, in which X is N—H, (R⁷)_(m) is 3-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 303

Compounds of the formula I.3A*, in which X is N—CH₃, (R⁷)_(m) is 3-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 304

Compounds of the formula I.3A*, in which X is N—C₂H₅, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 305

Compounds of the formula I.3A*, in which X is N-n-C₃H₇, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 306

Compounds of the formula I.3A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is3-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 307

Compounds of the formula I.3A*, in which X is N-n-C₄H₉, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 308

Compounds of the formula I.3A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is3-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 309

Compounds of the formula I.3A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 310

Compounds of the formula I.3A*, in which X is N—CH₂CN, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 311

Compounds of the formula I.3A*, in which X is N—CH₂CF₃, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 312

Compounds of the formula I.3A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 313

Compounds of the formula I.3A*, in which X is N—H, (R⁷)_(m) is 4-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 314

Compounds of the formula I.3A*, in which X is N—CH₃, (R⁷)_(m) is 4-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 315

Compounds of the formula I.3A*, in which X is N—C₂H₅, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 316

Compounds of the formula I.3A*, in which X is N-n-C₃H₇, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 317

Compounds of the formula I.3A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is4-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 318

Compounds of the formula I.3A*, in which X is N-n-C₄H₉, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 319

Compounds of the formula I.3A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is4-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 320

Compounds of the formula I.3A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 321

Compounds of the formula I.3A*, in which X is N—CH₂CN, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 322

Compounds of the formula I.3A*, in which X is N—CH₂CF₃, (RR⁷⁶)_(m) is4-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 323

Compounds of the formula I.3A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 324

Compounds of the formula I.3A*, in which X is N—H, (R⁷)_(m) is 5-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 325

Compounds of the formula I.3A*, in which X is N—CH₃, (R⁷)_(m) is 5-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 326

Compounds of the formula I.3A*, in which X is N—C₂H₅, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 327

Compounds of the formula I.3A*, in which X is N-n-C₃H₇, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 328

Compounds of the formula I.3A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is5-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 329

Compounds of the formula I.3A*, in which X is N-n-C₄H₉, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 330

Compounds of the formula I.3A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is5-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 331

Compounds of the formula I.3A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 332

Compounds of the formula I.3A*, in which X is N—CH₂CN, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 333

Compounds of the formula I.3A*, in which X is N—CH₂CF₃, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 334

Compounds of the formula I.3A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 335

Compounds of the formula I.3A*, in which X is N—H, (R⁷)_(m) is 6-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 336

Compounds of the formula I.3A*, in which X is N—CH₃, (R⁷)_(m) is 6-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 337

Compounds of the formula I.3A*, in which X is N—C₂H₅, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 338

Compounds of the formula I.3A*, in which X is N-n-C₃H₇, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 339

Compounds of the formula I.3A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is6-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 340

Compounds of the formula I.3A*, in which X is N-n-C₄H₉, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 341

Compounds of the formula I.3A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is6-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 342

Compounds of the formula I.3A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 343

Compounds of the formula I.3A*, in which X is N—CH₂CN, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 344

Compounds of the formula I.3A*, in which X is N—CH₂CF₃, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 345

Compounds of the formula I.3A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 346

Compounds of the formula I.3A*, in which X is N—H, (R⁷)_(m) is 4-CF₃ andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 347

Compounds of the formula I.3A*, in which X is N—CH₃, (R⁷)_(m) is 4-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 348

Compounds of the formula I.3A*, in which X is N—C₂H₅, (R⁷)_(m) is 4-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 349

Compounds of the formula I.3A*, in which X is N-n-C₃H₇, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 350

Compounds of the formula I.3A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 351

Compounds of the formula I.3A*, in which X is N-n-C₄H₉, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 352

Compounds of the formula I.3A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 353

Compounds of the formula I.3A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 354

Compounds of the formula I.3A*, in which X is N—CH₂CN, (R⁷)_(m) is 4-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 355

Compounds of the formula I.3A*, in which X is N—CH₂CF₃, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 356

Compounds of the formula I.3A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 357

Compounds of the formula I.3A*, in which X is N—H, (R⁷)_(m) is 5-CF₃ andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 358

Compounds of the formula I.3A*, in which X is N—CH₃, (R⁷)_(m) is 5-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 359

Compounds of the formula I.3A*, in which X is N—C₂H₅, (R⁷)_(m) is 5-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 360

Compounds of the formula I.3A*, in which X is N-n-C₃H₇, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 361

Compounds of the formula I.3A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 362

Compounds of the formula I.3A*, in which X is N-n-C₄H₉, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 363

Compounds of the formula I.3A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 364

Compounds of the formula I.3A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 365

Compounds of the formula I.3A*, in which X is N—CH₂CN, (R⁷)_(m) is 5-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 366

Compounds of the formula I.3A*, in which X is N—CH₂CF₃, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 367

Compounds of the formula I.3A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 368

Compounds of the formula I.3A*, in which X is N—H, (R⁷)_(m) is 3,6-F₂and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 369

Compounds of the formula I.3A*, in which X is N—CH₃, (R⁷)_(m) is 3,6-F₂and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 370

Compounds of the formula I.3A*, in which X is N—C₂H₅, (R⁷)_(m) is 3,6-F₂and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 371

Compounds of the formula I.3A*, in which X is N-n-C₃H₇, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 372

Compounds of the formula I.3A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 373

Compounds of the formula I.3A*, in which X is N-n-C₄H₉, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 374

Compounds of the formula I.3A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 375

Compounds of the formula I.3A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 376

Compounds of the formula I.3A*, in which X is N—CH₂CN, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 377

Compounds of the formula I.3A*, in which X is N—CH₂CF₃, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 378

Compounds of the formula I.3A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 379

Compounds of the formula I.4A*, in which X is oxygen, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 380

Compounds of the formula I.4A*, in which X is oxygen, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 381

Compounds of the formula I.4A*, in which X is oxygen, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 382

Compounds of the formula I.4A*, in which X is oxygen, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 383

Compounds of the formula I.4A*, in which X is oxygen, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 384

Compounds of the formula I.4A*, in which X is oxygen, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 385

Compounds of the formula I.4A*, in which X is oxygen, (R⁷)_(m) is 4-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 386

Compounds of the formula I.4A*, in which X is oxygen, (R⁷)_(m) is 5-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 387

Compounds of the formula I.4A*, in which X is oxygen, (R⁷)_(m) is 3,6-F₂and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 388

Compounds of the formula I.4A*, in which X is sulfur, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 389

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 390

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 391

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 392

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 393

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 394

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_(m) is 4-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 395

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_(m) is 5-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 396

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_(m) is 3,6-F₂and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 397

Compounds of the formula I.4A*, in which X is sulfur, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 398

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_(m) is 4-Cland the combination of Wand R⁶ for a compound corresponds in each caseto one row of Table A

Table 399

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_(m) is 3-Fand the combination of Wand R⁶ for a compound corresponds in each caseto one row of Table A

Table 400

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_(m) is 4-Fand the combination of Wand R⁶ for a compound corresponds in each caseto one row of Table A

Table 401

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 402

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 403

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_(m) is 4-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 404

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_(m) is 5-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 405

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_(m) is 3,6-F₂and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 406

Compounds of the formula I.4A*, in which X is N—H, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 407

Compounds of the formula I.4A*, in which X is N—CH₃, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 408

Compounds of the formula I.4A*, in which X is N—C₂H₅, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 409

Compounds of the formula I.4A*, in which X is N-n-C₃H₇, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 410

Compounds of the formula I.4A*, in which X is N—CH(CH₃)₂, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 411

Compounds of the formula I.4A*, in which X is N-n-C₄H₉, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 412

Compounds of the formula I.4A*, in which X is N—CH₂CH═CH₂, the index min (R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 413

Compounds of the formula I.4A*, in which X is N—CH₂C≡CH, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 414

Compounds of the formula I.4A*, in which X is N—CH₂CN, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 415

Compounds of the formula I.4A*, in which X is N—CH₂CF₃, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 416

Compounds of the formula I.4A*, in which X is N—CH₂C₆H₅, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 417

Compounds of the formula I.4A*, in which X is N—H, (R⁷)_(m) is 4-Cl andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 418

Compounds of the formula I.4A*, in which X is N—CH₃, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 419

Compounds of the formula I.4A*, in which X is N—C₂H₅, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 420

Compounds of the formula I.4A*, in which X is N-n-C₃H₇, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 421

Compounds of the formula I.4A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is4-Cl and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 422

Compounds of the formula I.4A*, in which X is N-n-C₄H₉, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 423

Compounds of the formula I.4A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is4-Cl and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 424

Compounds of the formula I.4A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is4-Cl and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 425

Compounds of the formula I.4A*, in which X is N—CH₂CN, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 426

Compounds of the formula I.4A*, in which X is N—CH₂CF₃, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 427

Compounds of the formula I.4A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is4-Cl and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 428

Compounds of the formula I.4A*, in which X is N—H, (R⁷)_(m) is 3-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 429

Compounds of the formula I.4A*, in which X is N—CH₃, (R⁷)_(m) is 3-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 430

Compounds of the formula I.4A*, in which X is N—C₂H₅, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 431

Compounds of the formula I.4A*, in which X is N-n-C₃H₇, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 432

Compounds of the formula I.4A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is3-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 433

Compounds of the formula I.4A*, in which X is N-n-C₄H₉, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 434

Compounds of the formula I.4A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is3-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 435

Compounds of the formula I.4A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 436

Compounds of the formula I.4A*, in which X is N—CH₂CN, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 437

Compounds of the formula I.4A*, in which X is N—CH₂CF₃, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 438

Compounds of the formula I.4A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 439

Compounds of the formula I.4A*, in which X is N—H, (R⁷)_(m) is 4-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 440

Compounds of the formula I.4A*, in which X is N—CH₃, (R⁷)_(m) is 4-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 441

Compounds of the formula I.4A*, in which X is N—C₂H₅, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 442

Compounds of the formula I.4A*, in which X is N-n-C₃H₇, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 443

Compounds of the formula I.4A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is4-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 444

Compounds of the formula I.4A*, in which X is N-n-C₄H₉, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 445

Compounds of the formula I.4A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is4-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 446

Compounds of the formula I.4A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 447

Compounds of the formula I.4A*, in which X is N—CH₂CN, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 448

Compounds of the formula I.4A*, in which X is N—CH₂CF₃, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 449

Compounds of the formula I.4A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 450

Compounds of the formula I.4A*, in which X is N—H, (R⁷)_(m) is 5-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 451

Compounds of the formula I.4A*, in which X is N—CH₃, (R⁷)_(m) is 5-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 452

Compounds of the formula I.4A*, in which X is N—C₂H₅, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 453

Compounds of the formula I.4A*, in which X is N-n-C₃H₇, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 454

Compounds of the formula I.4A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is5-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 455

Compounds of the formula I.4A*, in which X is N-n-C₄H₉, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 456

Compounds of the formula I.4A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is5-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 457

Compounds of the formula I.4A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 458

Compounds of the formula I.4A*, in which X is N—CH₂CN, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 459

Compounds of the formula I.4A*, in which X is N—CH₂CF₃, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 460

Compounds of the formula I.4A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 461

Compounds of the formula I.4A*, in which X is N—H, (R⁷)_(m) is 6-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 462

Compounds of the formula I.4A*, in which X is N—CH₃, (R⁷)_(m) is 6-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 463

Compounds of the formula I.4A*, in which X is N—C₂H₅, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 464

Compounds of the formula I.4A*, in which X is N-n-C₃H₇, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 465

Compounds of the formula I.4A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is6-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 466

Compounds of the formula I.4A*, in which X is N-n-C₄H₉, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 467

Compounds of the formula I.4A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is6-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 468

Compounds of the formula I.4A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 469

Compounds of the formula I.4A*, in which X is N—CH₂CN, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 470

Compounds of the formula I.4A*, in which X is N—CH₂CF₃, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 471

Compounds of the formula I.4A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 472

Compounds of the formula I.4A*, in which X is N—H, (R⁷)_(m) is 4-CF₃ andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 473

Compounds of the formula I.4A*, in which X is N—CH₃, (R⁷)_(m) is 4-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 474

Compounds of the formula I.4A*, in which X is N—C₂H₅, (R⁷)_(m) is 4-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 475

Compounds of the formula I.4A*, in which X is N-n-C₃H₇, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 476

Compounds of the formula I.4A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 477

Compounds of the formula I.4A*, in which X is N-n-C₄H₉, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 478

Compounds of the formula I.4A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 479

Compounds of the formula I.4A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 480

Compounds of the formula I.4A*, in which X is N—CH₂CN, (R⁷)_(m) is 4-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 481

Compounds of the formula I.4A*, in which X is N—CH₂CF₃, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 482

Compounds of the formula I.4A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 483

Compounds of the formula I.4A*, in which X is N—H, (R⁷)_(m) is 5-CF₃ andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 484

Compounds of the formula I.4A*, in which X is N—CH₃, (R⁷)_(m) is 5-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 485

Compounds of the formula I.4A*, in which X is N—C₂H₅, (R⁷)_(m) is 5-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 486

Compounds of the formula I.4A*, in which X is N-n-C₃H₇, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 487

Compounds of the formula I.4A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 488

Compounds of the formula I.4A*, in which X is N-n-C₄H₉, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 489

Compounds of the formula I.4A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 490

Compounds of the formula I.4A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 491

Compounds of the formula I.4A*, in which X is N—CH₂CN, (R⁷)_(m) is 5-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 492

Compounds of the formula I.4A*, in which X is N—CH₂CF₃, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 493

Compounds of the formula I.4A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 494

Compounds of the formula I.4A*, in which X is N—H, (R⁷)_(m) is 3,6-F₂and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 495

Compounds of the formula I.4A*, in which X is N—CH₃, (R⁷)_(m) is 3,6-F₂and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 496

Compounds of the formula I.4A*, in which X is N—C₂H₅, (R⁷)_(m) is 3,6-F₂and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 497

Compounds of the formula I.4A*, in which X is N-n-C₃H₇, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 498

Compounds of the formula I.4A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 499

Compounds of the formula I.4A*, in which X is N-n-C₄H₉, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 500

Compounds of the formula I.4A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 501

Compounds of the formula I.4A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 502

Compounds of the formula I.4A*, in which X is N—CH₂CN, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 503

Compounds of the formula I.4A*, in which X is N—CH₂CF₃, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 504

Compounds of the formula I.4A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 505

Compounds of the formula I.5A*, in which X is oxygen, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 506

Compounds of the formula I.5A*, in which X is oxygen, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 507

Compounds of the formula I.5A*, in which X is oxygen, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 508

Compounds of the formula I.5A*, in which X is oxygen, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 509

Compounds of the formula I.5A*, in which X is oxygen, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 510

Compounds of the formula I.5A*, in which X is oxygen, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 511

Compounds of the formula I.5A*, in which X is oxygen, (R⁷)_(m) is 4-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 512

Compounds of the formula I.5A*, in which X is oxygen, (R⁷)_(m) is 5-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 513

Compounds of the formula I.5A*, in which X is oxygen, (R⁷)_(m) is 3,6-F₂and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 514

Compounds of the formula I.5A*, in which X is sulfur, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 515

Compounds of the formula I.5A*, in which X is sulfur, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 516

Compounds of the formula I.5A*, in which X is sulfur, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 517

Compounds of the formula I.5A*, in which X is sulfur, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 518

Compounds of the formula I.5A*, in which X is sulfur, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 519

Compounds of the formula I.5A*, in which X is sulfur, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 520

Compounds of the formula I.5A*, in which X is sulfur, (R⁷)_(m) is 4-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 521

Compounds of the formula I.5A*, in which X is sulfur, (R⁷)_(m) is 5-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 522

Compounds of the formula I.5A*, in which X is sulfur, (R⁷)_(m) is 3,6-F₂and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 523

Compounds of the formula I.5A*, in which X is sulfur, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 524

Compounds of the formula I.5A*, in which X is sulfur, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 525

Compounds of the formula I.5A*, in which X is sulfur, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 526

Compounds of the formula I.5A*, in which X is sulfur, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 527

Compounds of the formula I.5A*, in which X is sulfur, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 528

Compounds of the formula I.5A*, in which X is sulfur, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 529

Compounds of the formula I.5A*, in which X is sulfur, (RR⁷⁶)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 530

Compounds of the formula I.5A*, in which X is sulfur, (R⁷)_(m) is 5-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 531

Compounds of the formula I.5A*, in which X is sulfur, (R⁷)_(m) is 3,6-F₂and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 532

Compounds of the formula I.5A*, in which X is N—H, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 533

Compounds of the formula I.5A*, in which X is N—CH₃, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 534

Compounds of the formula I.5A*, in which X is N—C₂H₅, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 535

Compounds of the formula I.5A*, in which X is N-n-C₃H₇, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 536

Compounds of the formula I.5A*, in which X is N—CH(CH₃)₂, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 537

Compounds of the formula I.5A*, in which X is N-n-C₄H₉, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 538

Compounds of the formula I.5A*, in which X is N—CH₂CH═CH₂, the index min (R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 539

Compounds of the formula I.5A*, in which X is N—CH₂C≡CH, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 540

Compounds of the formula I.5A*, in which X is N—CH₂CN, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 541

Compounds of the formula I.5A*, in which X is N—CH₂CF₃, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 542

Compounds of the formula I.5A*, in which X is N—CH₂C₆H₅, the index m in(R⁷)_(m) is zero and the combination of R¹ and R⁶ for a compoundcorresponds in each case to one row of Table A

Table 543

Compounds of the formula I.5A*, in which X is N—H, (R⁷)_(m) is 4-Cl andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 544

Compounds of the formula I.5A*, in which X is N—CH₃, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 545

Compounds of the formula I.5A*, in which X is N—C₂H₅, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 546

Compounds of the formula I.5A*, in which X is N-n-C₃H₇, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 547

Compounds of the formula I.5A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is4-Cl and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 548

Compounds of the formula I.5A*, in which X is N-n-C₄H₉, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 549

Compounds of the formula I.5A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is4-Cl and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 550

Compounds of the formula I.5A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is4-Cl and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 551

Compounds of the formula I.5A*, in which X is N—CH₂CN, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 552

Compounds of the formula I.5A*, in which X is N—CH₂CF₃, (R⁷)_(m) is 4-Cland the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 553

Compounds of the formula I.5A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is4-Cl and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 554

Compounds of the formula I.5A*, in which X is N—H, (R⁷)_(m) is 3-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 555

Compounds of the formula I.5A*, in which X is N—CH₃, (R⁷)_(m) is 3-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 556

Compounds of the formula I.5A*, in which X is N—C₂H₅, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 557

Compounds of the formula I.5A*, in which X is N-n-C₃H₇, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 558

Compounds of the formula I.5A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is3-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 559

Compounds of the formula I.5A*, in which X is N-n-C₄H₉, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 560

Compounds of the formula I.5A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is3-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 561

Compounds of the formula I.5A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 562

Compounds of the formula I.5A*, in which X is N—CH₂CN, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 563

Compounds of the formula I.5A*, in which X is N—CH₂CF₃, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 564

Compounds of the formula I.5A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is 3-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 565

Compounds of the formula I.5A*, in which X is N—H, (R⁷)_(m) is 4-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 566

Compounds of the formula I.5A*, in which X is N—CH₃, (R⁷)_(m) is 4-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 567

Compounds of the formula I.5A*, in which X is N—C₂H₅, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 568

Compounds of the formula I.5A*, in which X is N-n-C₃H₇, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 569

Compounds of the formula I.5A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is4-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 570

Compounds of the formula I.5A*, in which X is N-n-C₄H₉, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 571

Compounds of the formula I.5A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is4-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 572

Compounds of the formula I.5A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 573

Compounds of the formula I.5A*, in which X is N—CH₂CN, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 574

Compounds of the formula I.5A*, in which X is N—CH₂CF₃, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 575

Compounds of the formula I.5A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is 4-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 576

Compounds of the formula I.5A*, in which X is N—H, (R⁷)_(m) is 5-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 577

Compounds of the formula I.5A*, in which X is N—CH₃, (R⁷)_(m) is 5-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 578

Compounds of the formula I.5A*, in which X is N—C₂H₅, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 579

Compounds of the formula I.5A*, in which X is N-n-C₃H₇, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 580

Compounds of the formula I.5A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is5-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 581

Compounds of the formula I.5A*, in which X is N-n-C₄H₉, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 582

Compounds of the formula I.5A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is5-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 583

Compounds of the formula I.5A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 584

Compounds of the formula I.5A*, in which X is N—CH₂CN, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 585

Compounds of the formula I.5A*, in which X is N—CH₂CF₃, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 586

Compounds of the formula I.5A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is 5-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 587

Compounds of the formula I.5A*, in which X is N—H, (R⁷)_(m) is 6-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 588

Compounds of the formula I.5A*, in which X is N—CH₃, (R⁷)_(m) is 6-F andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 589

Compounds of the formula I.5A*, in which X is N—C₂H₅, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 590

Compounds of the formula I.5A*, in which X is N-n-C₃H₇, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 591

Compounds of the formula I.5A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is6-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 592

Compounds of the formula I.5A*, in which X is N-n-C₄H₉, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 593

Compounds of the formula I.5A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is6-F and the combination of R¹ and R⁶ for a compound corresponds in eachcase to one row of Table A

Table 594

Compounds of the formula I.5A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 595

Compounds of the formula I.5A*, in which X is N—CH₂CN, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 596

Compounds of the formula I.5A*, in which X is N—CH₂CF₃, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 597

Compounds of the formula I.5A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is 6-Fand the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 598

Compounds of the formula I.5A*, in which X is N—H, (R⁷)_(m) is 4-CF₃ andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 599

Compounds of the formula I.5A*, in which X is N—CH₃, (R⁷)_(m) is 4-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 600

Compounds of the formula I.5A*, in which X is N—C₂H₅, (R⁷)_(m) is 4-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 601

Compounds of the formula I.5A*, in which X is N-n-C₃H₇, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 602

Compounds of the formula I.5A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 603

Compounds of the formula I.5A*, in which X is N-n-C₄H₉, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 604

Compounds of the formula I.5A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 605

Compounds of the formula I.5A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 606

Compounds of the formula I.5A*, in which X is N—CH₂CN, (R⁷)_(m) is 4-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 607

Compounds of the formula I.5A*, in which X is N—CH₂CF₃, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 608

Compounds of the formula I.5A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 609

Compounds of the formula I.5A*, in which X is N—H, (R⁷)_(m) is 5-CF₃ andthe combination of R¹ and R⁶ for a compound corresponds in each case toone row of Table A

Table 610

Compounds of the formula I.5A*, in which X is N—CH₃, (R⁷)_(m) is 5-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 611

Compounds of the formula I.5A*, in which X is N—C₂H₅, (R⁷)_(m) is 5-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 612

Compounds of the formula I.5A*, in which X is N-n-C₃H₇, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 613

Compounds of the formula I.5A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 614

Compounds of the formula I.5A*, in which X is N-n-C₄H₉, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 615

Compounds of the formula I.5A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 616

Compounds of the formula I.5A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 617

Compounds of the formula I.5A*, in which X is N—CH₂CN, (R⁷)_(m) is 5-CF₃and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 618

Compounds of the formula I.5A*, in which X is N—CH₂CF₃, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 619

Compounds of the formula I.5A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 620

Compounds of the formula I.5A*, in which X is N—H, (R⁷)_(m) is 3,6-F₂and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 621

Compounds of the formula I.5A*, in which X is N—CH₃, (R⁷)_(m) is 3,6-F₂and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 622

Compounds of the formula I.5A*, in which X is N—C₂H₅, (R⁷)_(m) is 3,6-F₂and the combination of R¹ and R⁶ for a compound corresponds in each caseto one row of Table A

Table 623

Compounds of the formula I.5A*, in which X is N-n-C₃H₇, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 624

Compounds of the formula I.5A*, in which X is N—CH(CH₃)₂, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 625

Compounds of the formula I.5A*, in which X is N-n-C₄H₉, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 626

Compounds of the formula I.5A*, in which X is N—CH₂CH═CH₂, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 627

Compounds of the formula I.5A*, in which X is N—CH₂C≡CH, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 628

Compounds of the formula I.5A*, in which X is N—CH₂CN, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 629

Compounds of the formula I.5A*, in which X is N—CH₂CF₃, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

Table 630

Compounds of the formula I.5A*, in which X is N—CH₂C₆H₅, (R⁷)_(m) is3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds ineach case to one row of Table A

No. R¹ R⁶ A-1 OH Br A-2 OCH₃ Br A-3 OC(O)CH₃ Br A-4 OC(O)CH₂CH₃ Br A-5OC(O)CH(CH₃)₂ Br A-6 OC(O)C(CH₃)₃ Br A-7 OC(O)-c-C₃H₅ Br A-8 OC(O)—C₆H₅Br A-9 OC(O)—CH₂C₆H₅ Br A-10 OC(O)CH₂Cl Br A-11 OC(O)—CF₃ Br A-12OC(O)—CH₂OCH₃ Br A-13 OC(O)—N(CH₃)₂ Br A-14 OC(O)—OCH₂CH₃ Br A-15OS(O)₂—CH₃ Br A-16 OS(O)₂—C₂H₅ Br A-17 OS(O)₂—C₃H₇ Br A-18OS(O)₂—CH(CH₃)₂ Br A-19 OS(O)₂—C₆H₅ Br A-20 OS(O)₂—T1 Br A-21 OS(O)₂—T2Br A-22 OS(O)₂—T3 Br A-23 OS(O)₂—T4 Br A-24 OS(O)₂—T5 Br A-25 OS(O)₂—T6Br A-26 OS(O)₂—T7 Br A-27 OS(O)₂—T8 Br A-28 OS(O)₂—T9 Br A-29 OS(O)₂—T10Br A-30 OS(O)₂—T11 Br A-31 OS(O)₂—T12 Br A-32 OH Cl A-33 OCH₃ Cl A-34OC(O)CH₃ Cl A-35 OC(O)CH₂CH₃ Cl A-36 OC(O)CH(CH₃)₂ Cl A-37 OC(O)C(CH₃)₃Cl A-38 OC(O)-c-C₃H₅ Cl A-39 OC(O)—C₆H₅ Cl A-40 OC(O)—CH₂C₆H₅ Cl A-41OC(O)CH₂Cl Cl A-42 OC(O)—CF₃ Cl A-43 OC(O)—CH₂OCH₃ Cl A-44 OC(O)—N(CH₃)₂Cl A-45 OC(O)—OCH₂CH₃ Cl A-46 OS(O)₂—CH₃ Cl A-47 OS(O)₂—C₂H₅ Cl A-48OS(O)₂—C₃H₇ Cl A-49 OS(O)₂—CH(CH₃)₂ Cl A-50 OS(O)₂—C₆H₅ Cl A-51OS(O)₂—T1 Cl A-52 OS(O)₂—T2 Cl A-53 OS(O)₂—T3 Cl A-54 OS(O)₂—T4 Cl A-55OS(O)₂—T5 Cl A-56 OS(O)₂—T6 Cl A-57 OS(O)₂—T7 Cl A-58 OS(O)₂—T8 Cl A-59OS(O)₂—T9 Cl A-60 OS(O)₂—T10 Cl A-61 OS(O)₂—T11 Cl A-62 OS(O)₂—T12 ClA-63 OH F A-64 OCH₃ F A-65 OC(O)CH₃ F A-66 OC(O)CH₂CH₃ F A-67OC(O)CH(CH₃)₂ F A-68 OC(O)C(CH₃)₃ F A-69 OC(O)-c-C₃H₅ F A-70 OC(O)—C₆H₅F A-71 OC(O)—CH₂C₆H₅ F A-72 OC(O)CH₂Cl F A-73 OC(O)—CF₃ F A-74OC(O)—CH₂OCH₃ F A-75 OC(O)—N(CH₃)₂ F A-76 OC(O)—OCH₂CH₃ F A-77OS(O)₂—CH₃ F A-78 OS(O)₂—C₂H₅ F A-79 OS(O)₂—C₃H₇ F A-80 OS(O)₂—CH(CH₃)₂F A-81 OS(O)₂—C₆H₅ F A-82 OS(O)₂—T1 F A-83 OS(O)₂—T2 F A-84 OS(O)₂—T3 FA-85 OS(O)₂—T4 F A-86 OS(O)₂—T5 F A-87 OS(O)₂—T6 F A-88 OS(O)₂—T7 F A-89OS(O)₂—T8 F A-90 OS(O)₂—T9 F A-91 OS(O)₂—T10 F A-92 OS(O)₂—T11 F A-93OS(O)₂—T12 F A-94 OH NO₂ A-95 OCH₃ NO₂ A-96 OC(O)CH₃ NO₂ A-97OC(O)CH₂CH₃ NO₂ A-98 OC(O)CH(CH₃)₂ NO₂ A-99 OC(O)C(CH₃)₃ NO₂ A-100OC(O)-c-C₃H₅ NO₂ A-101 OC(O)—C₆H₅ NO₂ A-102 OC(O)—CH₂C₆H₅ NO₂ A-103OC(O)CH₂Cl NO₂ A-104 OC(O)—CF₃ NO₂ A-105 OC(O)—CH₂OCH₃ NO₂ A-106OC(O)—N(CH₃)₂ NO₂ A-107 OC(O)—OCH₂CH₃ NO₂ A-108 OS(O)₂—CH₃ NO₂ A-109OS(O)₂—C₂H₅ NO₂ A-110 OS(O)₂—C₃H₇ NO₂ A-111 OS(O)₂—CH(CH₃)₂ NO₂ A-112OS(O)₂—C₆H₅ NO₂ A-113 OS(O)₂—T1 NO₂ A-114 OS(O)₂—T2 NO₂ A-115 OS(O)₂—T3NO₂ A-116 OS(O)₂—T4 NO₂ A-117 OS(O)₂—T5 NO₂ A-118 OS(O)₂—T6 NO₂ A-119OS(O)₂—T7 NO₂ A-120 OS(O)₂—T8 NO₂ A-121 OS(O)₂—T9 NO₂ A-122 OS(O)₂—T10NO₂ A-123 OS(O)₂—T11 NO₂ A-124 OS(O)₂—T12 NO₂ A-125 OH CN A-126 OCH₃ CNA-127 OC(O)CH₃ CN A-128 OC(O)CH₂CH₃ CN A-129 OC(O)CH(CH₃)₂ CN A-130OC(O)C(CH₃)₃ CN A-131 OC(O)-c-C₃H₅ CN A-132 OC(O)—C₆H₅ CN A-133OC(O)—CH₂C₆H₅ CN A-134 OC(O)CH₂Cl CN A-135 OC(O)—CF₃ CN A-136OC(O)—CH₂OCH₃ CN A-137 OC(O)—N(CH₃)₂ CN A-138 OC(O)—OCH₂CH₃ CN A-139OS(O)₂—CH₃ CN A-140 OS(O)₂—C₂H₅ CN A-141 OS(O)₂—C₃H₇ CN A-142OS(O)₂—CH(CH₃)₂ CN A-143 OS(O)₂—C₆H₅ CN A-144 OS(O)₂—T1 CN A-145OS(O)₂—T2 CN A-146 OS(O)₂—T3 CN A-147 OS(O)₂—T4 CN A-148 OS(O)₂—T5 CNA-149 OS(O)₂—T6 CN A-150 OS(O)₂—T7 CN A-151 OS(O)₂—T8 CN A-152 OS(O)₂—T9CN A-153 OS(O)₂—T10 CN A-154 OS(O)₂—T11 CN A-155 OS(O)₂—T12 CN A-156 OHCH₃ A-157 OCH₃ CH₃ A-158 OC(O)CH₃ CH₃ A-159 OC(O)CH₂CH₃ CH₃ A-160OC(O)CH(CH₃)₂ CH₃ A-161 OC(O)C(CH₃)₃ CH₃ A-162 OC(O)-c-C₃H₅ CH₃ A-163OC(O)—C₆H₅ CH₃ A-164 OC(O)—CH₂C₆H₅ CH₃ A-165 OC(O)CH₂Cl CH₃ A-166OC(O)—CF₃ CH₃ A-167 OC(O)—CH₂OCH₃ CH₃ A-168 OC(O)—N(CH₃)₂ CH₃ A-169OC(O)—OCH₂CH₃ CH₃ A-170 OS(O)₂—CH₃ CH₃ A-171 OS(O)₂—C₂H₅ CH₃ A-172OS(O)₂—C₃H₇ CH₃ A-173 OS(O)₂—CH(CH₃)₂ CH₃ A-174 OS(O)₂—C₆H₅ CH₃ A-175OS(O)₂—T1 CH₃ A-176 OS(O)₂—T2 CH₃ A-177 OS(O)₂—T3 CH₃ A-178 OS(O)₂—T4CH₃ A-179 OS(O)₂—T5 CH₃ A-180 OS(O)₂—T6 CH₃ A-181 OS(O)₂—T7 CH₃ A-182OS(O)₂—T8 CH₃ A-183 OS(O)₂—T9 CH₃ A-184 OS(O)₂—T10 CH₃ A-185 OS(O)₂—T11CH₃ A-186 OS(O)₂—T12 CH₃ A-187 OH OCH₃ A-188 OCH₃ OCH₃ A-189 OC(O)CH₃OCH₃ A-190 OC(O)CH₂CH₃ OCH₃ A-191 OC(O)CH(CH₃)₂ OCH₃ A-192 OC(O)C(CH₃)₃OCH₃ A-193 OC(O)-c-C₃H₅ OCH₃ A-194 OC(O)—C₆H₅ OCH₃ A-195 OC(O)—CH₂C₆H₅OCH₃ A-196 OC(O)CH₂Cl OCH₃ A-197 OC(O)—CF₃ OCH₃ A-198 OC(O)—CH₂OCH₃ OCH₃A-199 OC(O)—N(CH₃)₂ OCH₃ A-200 OC(O)—OCH₂CH₃ OCH₃ A-201 OS(O)₂—CH₃ OCH₃A-202 OS(O)₂—C₂H₅ OCH₃ A-203 OS(O)₂—C₃H₇ OCH₃ A-204 OS(O)₂—CH(CH₃)₂ OCH₃A-205 OS(O)₂—C₆H₅ OCH₃ A-206 OS(O)₂—T1 OCH₃ A-207 OS(O)₂—T2 OCH₃ A-208OS(O)₂—T3 OCH₃ A-209 OS(O)₂—T4 OCH₃ A-210 OS(O)₂—T5 OCH₃ A-211 OS(O)₂—T6OCH₃ A-212 OS(O)₂—T7 OCH₃ A-213 OS(O)₂—T8 OCH₃ A-214 OS(O)₂—T9 OCH₃A-215 OS(O)₂—T10 OCH₃ A-216 OS(O)₂—T11 OCH₃ A-217 OS(O)₂—T12 OCH₃ A-218OH CHF₂ A-219 OCH₃ CHF₂ A-220 OC(O)CH₃ CHF₂ A-221 OC(O)CH₂CH₃ CHF₂ A-222OC(O)CH(CH₃)₂ CHF₂ A-223 OC(O)C(CH₃)₃ CHF₂ A-224 OC(O)-c-C₃H₅ CHF₂ A-225OC(O)—C₆H₅ CHF₂ A-226 OC(O)—CH₂C₆H₅ CHF₂ A-227 OC(O)CH₂Cl CHF₂ A-228OC(O)—CF₃ CHF₂ A-229 OC(O)—CH₂OCH₃ CHF₂ A-230 OC(O)—N(CH₃)₂ CHF₂ A-231OC(O)—OCH₂CH₃ CHF₂ A-232 OS(O)₂—CH₃ CHF₂ A-233 OS(O)₂—C₂H₅ CHF₂ A-234OS(O)₂—C₃H₇ CHF₂ A-235 OS(O)₂—CH(CH₃)₂ CHF₂ A-236 OS(O)₂—C₆H₅ CHF₂ A-237OS(O)₂—T1 CHF₂ A-238 OS(O)₂—T2 CHF₂ A-239 OS(O)₂—T3 CHF₂ A-240 OS(O)₂—T4CHF₂ A-241 OS(O)₂—T5 CHF₂ A-242 OS(O)₂—T6 CHF₂ A-243 OS(O)₂—T7 CHF₂A-244 OS(O)₂—T8 CHF₂ A-245 OS(O)₂—T9 CHF₂ A-246 OS(O)₂—T10 CHF₂ A-247OS(O)₂—T11 CHF₂ A-248 OS(O)₂—T12 CHF₂ A-249 OH CF₃ A-250 OCH₃ CF₃ A-251OC(O)CH₃ CF₃ A-252 OC(O)CH₂CH₃ CF₃ A-253 OC(O)CH(CH₃)₂ CF₃ A-254OC(O)C(CH₃)₃ CF₃ A-255 OC(O)-c-C₃H₅ CF₃ A-256 OC(O)—C₆H₅ CF₃ A-257OC(O)—CH₂C₆H₅ CF₃ A-258 OC(O)CH₂Cl CF₃ A-259 OC(O)—CF₃ CF₃ A-260OC(O)—CH₂OCH₃ CF₃ A-261 OC(O)—N(CH₃)₂ CF₃ A-262 OC(O)—OCH₂CH₃ CF₃ A-263OS(O)₂—CH₃ CF₃ A-264 OS(O)₂—C₂H₅ CF₃ A-265 OS(O)₂—C₃H₇ CF₃ A-266OS(O)₂—CH(CH₃)₂ CF₃ A-267 OS(O)₂—C₆H₅ CF₃ A-268 OS(O)₂—T1 CF₃ A-269OS(O)₂—T2 CF₃ A-270 OS(O)₂—T3 CF₃ A-271 OS(O)₂—T4 CF₃ A-272 OS(O)₂—T5CF₃ A-273 OS(O)₂—T6 CF₃ A-274 OS(O)₂—T7 CF₃ A-275 OS(O)₂—T8 CF₃ A-276OS(O)₂—T9 CF₃ A-277 OS(O)₂—T10 CF₃ A-278 OS(O)₂—T11 CF₃ A-279 OS(O)₂—T12CF₃ A-280 OH OCHF₂ A-281 OCH₃ OCHF₂ A-282 OC(O)CH₃ OCHF₂ A-283OC(O)CH₂CH₃ OCHF₂ A-284 OC(O)CH(CH₃)₂ OCHF₂ A-285 OC(O)C(CH₃)₃ OCHF₂A-286 OC(O)-c-C₃H₅ OCHF₂ A-287 OC(O)—C₆H₅ OCHF₂ A-288 OC(O)—CH₂C₆H₅OCHF₂ A-289 OC(O)CH₂Cl OCHF₂ A-290 OC(O)—CF₃ OCHF₂ A-291 OC(O)—CH₂OCH₃OCHF₂ A-292 OC(O)—N(CH₃)₂ OCHF₂ A-293 OC(O)—OCH₂CH₃ OCHF₂ A-294OS(O)₂—CH₃ OCHF₂ A-295 OS(O)₂—C₂H₅ OCHF₂ A-296 OS(O)₂—C₃H₇ OCHF₂ A-297OS(O)₂—CH(CH₃)₂ OCHF₂ A-298 OS(O)₂—C₆H₅ OCHF₂ A-299 OS(O)₂—T1 OCHF₂A-300 OS(O)₂—T2 OCHF₂ A-301 OS(O)₂—T3 OCHF₂ A-302 OS(O)₂—T4 OCHF₂ A-303OS(O)₂—T5 OCHF₂ A-304 OS(O)₂—T6 OCHF₂ A-305 OS(O)₂—T7 OCHF₂ A-306OS(O)₂—T8 OCHF₂ A-307 OS(O)₂—T9 OCHF₂ A-308 OS(O)₂—T10 OCHF₂ A-309OS(O)₂—T11 OCHF₂ A-310 OS(O)₂—T12 OCHF₂ A-311 OH OCF₃ A-312 OCH₃ OCF₃A-313 OC(O)CH₃ OCF₃ A-314 OC(O)CH₂CH₃ OCF₃ A-315 OC(O)CH(CH₃)₂ OCF₃A-316 OC(O)C(CH₃)₃ OCF₃ A-317 OC(O)-c-C₃H₅ OCF₃ A-318 OC(O)—C₆H₅ OCF₃A-319 OC(O)—CH₂C₆H₅ OCF₃ A-320 OC(O)CH₂Cl OCF₃ A-321 OC(O)—CF₃ OCF₃A-322 OC(O)—CH₂OCH₃ OCF₃ A-323 OC(O)—N(CH₃)₂ OCF₃ A-324 OC(O)—OCH₂CH₃OCF₃ A-325 OS(O)₂—CH₃ OCF₃ A-326 OS(O)₂—C₂H₅ OCF₃ A-327 OS(O)₂—C₃H₇ OCF₃A-328 OS(O)₂—CH(CH₃)₂ OCF₃ A-329 OS(O)₂—C₆H₅ OCF₃ A-330 OS(O)₂—T1 OCF₃A-331 OS(O)₂—T2 OCF₃ A-332 OS(O)₂—T3 OCF₃ A-333 OS(O)₂—T4 OCF₃ A-334OS(O)₂—T5 OCF₃ A-335 OS(O)₂—T6 OCF₃ A-336 OS(O)₂—T7 OCF₃ A-337 OS(O)₂—T8OCF₃ A-338 OS(O)₂—T9 OCF₃ A-339 OS(O)₂—T10 OCF₃ A-340 OS(O)₂—T11 OCF₃A-341 OS(O)₂—T12 OCF₃ T1 = NH(4-CH₃—C₆H₄) T2 = N(CH₃)₂ T3 = N(CH₃)CH₂CH₃T4 = N(CH₃)C₃H₇ T5 = N(CH₃)CH(CH₃)₂ T6 = NH(2-Cl-6-COOH—C₆H₃) T7 =NH(2,6-Cl₂—C₆H₃) T8 = NH(2,6-F₂—C₆H₃) T9 = NH(2,6-Cl₂-3-CH₃—C₆H₂) T10 =NH(2-CF₃-6-CH₂CHF₂—C₆H₃) T11 = NH(2-CF₃-6-OCF₃—C₆H₃) T12 =NH(2-CF₃-6-OCH₂CHF₂—C₆H₃)

The compounds I and their agriculturally useful salts are suitable, bothas isomer mixtures and in the form of the pure isomers, as herbicides.They are suitable as such or as an appropriately formulated composition.The herbicidal compositions comprising the compound I, in particular thepreferred aspects thereof, control vegetation on non-crop areas veryefficiently, especially at high rates of application. They act againstbroad-leaved weeds and weed grasses in crops such as wheat, rice, corn,soybeans and cotton without causing any significant damage to the cropplants. This effect is mainly observed at low rates of application.

Depending on the application method in question, the compounds I, inparticular the preferred aspects thereof, or compositions comprisingthem can additionally be employed in a further number of crop plants foreliminating unwanted plants. Examples of suitable crops are thefollowing:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis,Avena sativa, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa,Brassica napus var. napus, Brassica napus var. napobrassica, Brassicarapa var. silvestris, Brassica oleracea, Brassica nigra, Camelliasinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon,Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica),Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis,Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum,Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Heveabrasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglansregia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum,Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotianatabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus,Phaseolus vulgaris, Picea abies, Pinus spec., Pistacia vera, Pisumsativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca,Prunus cerasus, Prunus dulcis and Prunus domestica, Ribes sylvestre,Ricinus communis, Saccharum officinarum, Secale cereale, Sinapis alba,Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao,Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Viciafaba, Vitis vinifera, Zea mays.

The term “crop plants” also includes plants which have been modified bybreeding, mutagenesis or genetic engineering. Genetically modifiedplants are plants whose genetic material has been modified in a mannerwhich does not occur under natural conditions by crossing, mutations ornatural recombination (i.e. reassembly of the genetic information).Here, in general, one or more genes are integrated into the geneticmaterial of the plant to improve the properties of the plant.

Accordingly, the term “crop plants” also includes plants which, bybreeding and genetic engineering, have acquired tolerance to certainclasses of herbicides, such as hydroxyphenylpyruvate dioxygenase (HPPD)inhibitors, acetolactate synthase (ALS) inhibitors, such as, forexample, sulfonylureas (EP-A 257 993, U.S. Pat. No. 5,013,659) orimidazolinones (see, for example, U.S. Pat. No. 6,222,100, WO 01/82685,WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073),enolpyruvylshikimate 3-phosphate synthase (EPSPS) inhibitors, such as,for example, glyphosate (see, for example, WO 92/00377), glutaminesynthetase (GS) inhibitors, such as, for example, glufosinate (see, forexample, EP-A 242 236, EP-A 242 246), or oxynil herbicides (see, forexample, U.S. Pat. No. 5,559,024).

Numerous crop plants, for example Clearfield® oilseed rape, tolerant toimidazolinones, for example imazamox, have been generated with the aidof classic breeding methods (mutagenesis). Crop plants such as soybeans,cotton, corn, beet and oilseed rape, resistant to glyphosate orglufosinate, which are available under the tradenames RoundupReady®(glyphosate) and Liberty Link® (glufosinate) have been generated withthe aid of genetic engineering methods.

Accordingly, the term “crop plants” also includes plants which, with theaid of genetic engineering, produce one or more toxins, for examplethose of the bacterial strain Bacillus ssp. Toxins which are produced bysuch genetically modified plants include, for example, insecticidalproteins of Bacillus spp., in particular B. thuringiensis, such as theendotoxins Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1,Cry9c, Cry34Ab1 or Cry35Ab1; or vegetative insecticidal proteins (VIPs),for example VIP1, VIP2, VIP3, or VIP3A; insecticidal proteins ofnematode-colonizing bacteria, for example Photorhabdus spp. orXenorhabdus spp.; toxins of animal organisms, for example wasp, spideror scorpion toxins; fungal toxins, for example from Streptomycetes;plant lectins, for example from peas or barley; agglutinins; proteinaseinhibitors, for example trypsin inhibitors, serine protease inhibitors,patatin, cystatin or papain inhibitors, ribosome-inactivating proteins(RIPs), for example ricin, corn-RIP, abrin, luffin, saporin or bryodin;steroid-metabolizing enzymes, for example 3-hydroxysteroid oxidase,ecdysteroid-IDP glycosyl transferase, cholesterol oxidase, ecdysoneinhibitors, or HMG-CoA reductase; ion channel blockers, for exampleinhibitors of sodium channels or calcium channels; juvenile hormoneesterase; receptors of the diuretic hormone (helicokinin receptors);stilbene synthase, bibenzyl synthase, chitinases and glucanases. In theplants, these toxins may also be produced as pretoxins, hybrid proteinsor truncated or otherwise modified proteins. Hybrid proteins arecharacterized by a novel combination of different protein domains (see,for example, WO 2002/015701). Further examples of such toxins orgenetically modified plants which produce these toxins are disclosed inEP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO03/018810 and WO 03/052073. The methods for producing these geneticallymodified plants are known to the person skilled in the art anddisclosed, for example, in the publications mentioned above. Numerous ofthe toxins mentioned above bestow, upon the plants by which they areproduced, tolerance to pests from all taxonomic classes of arthropods,in particular to beetles (Coeleropta), dipterans (Diptera) andbutterflies (Lepidoptera) and to nematodes (Nematoda).

Genetically modified plants which produce one or more genes coding forinsecticidal toxins are described, for example, in the publicationsmentioned above, and some of them are commercially available, such as,for example, YieldGard® (corn varieties producing the toxin Cry1Ab),YieldGard® Plus (corn varieties which produce the toxins Cry1Ab andCry3Bb1), Starlink® (corn varieties which produce the toxin Cry9c),Herculex® RW (corn varieties which produce the toxins Cry34Ab1, Cry35Ab1and the enzyme phosphinothricin-N-acetyltransferase [PAT]); NuCOTN® 33B(cotton varieties which produce the toxin Cry1Ac), Bollgard® I (cottonvarieties which produce the toxin Cry1Ac), Bollgard® II (cottonvarieties which produce the toxins Cry1Ac and Cry2Ab2); VIPCOT® (cottonvarieties which produce a VIP toxin); NewLeaf° (potato varieties whichproduce the toxin Cry3A); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®,Protecta®, Bt11 (for example Agrisure® CB) and Bt176 from Syngenta SeedsSAS, France (corn varieties which produce the toxin Cry1Ab and the PATenzyme), MIR604 from Syngenta Seeds SAS, France (corn varieties whichproduce a modified version of the toxin Cry3A, see WO 03/018810), MON863 from Monsanto Europe S.A., Belgium (corn varieties which produce thetoxin Cry3Bb1), IPC 531 from Monsanto Europe S.A., Belgium (cottonvarieties which produce a modified version of the toxin Cry1Ac) and 1507from Pioneer Overseas Corporation, Belgium (corn varieties which producethe toxin Cry1F and the PAT enzyme).

Accordingly, the term “crop plants” also includes plants which, with theaid of genetic engineering, produce one or more proteins which are morerobust or have increased resistance to bacterial, viral or fungalpathogens, such as, for example, pathogenesis-related proteins (PRproteins, see EP-A 0 392 225), resistance proteins (for example potatovarieties producing two resistance genes against Phytophthora infestansfrom the wild Mexican potato Solanum bulbocastanum) or T4 lysozyme (forexample potato cultivars which, by producing this protein, are resistantto bacteria such as Erwinia amylvora).

Accordingly, the term “crop plants” also includes plants whoseproductivity has been improved with the aid of genetic engineeringmethods, for example by enhancing the potential yield (for examplebiomass, grain yield, starch, oil or protein content), tolerance todrought, salt or other limiting environmental factors or resistance topests and fungal, bacterial and viral pathogens.

The term “crop plants” also includes plants whose ingredients have beenmodified with the aid of genetic engineering methods in particular forimproving human or animal diet, for example by oil plants producinghealth-promoting long-chain omega 3 fatty acids or monounsaturated omega9 fatty acids (for example Nexera® oilseed rape).

The term “crop plants” also includes plants which have been modifiedwith the aid of genetic engineering methods for improving the productionof raw materials, for example by increasing the amylopectin content ofpotatoes (Amflora® potato).

Furthermore, it has been found that the compounds of the formula I arealso suitable for the defoliation and/or desiccation of plant parts, forwhich crop plants such as cotton, potato, oilseed rape, sunflower,soybean or field beans, in particular cotton, are suitable. In thisregard, there have been found compositions for the desiccation and/ordefoliation of plants, processes for preparing these compositions andmethods for desiccating and/or defoliating plants using the compounds ofthe formula I.

As desiccants, the compounds of the formula I are particularly suitablefor desiccating the above-ground parts of crop plants such as potato,oilseed rape, sunflower and soybean, but also cereals. This makespossible the fully mechanical harvesting of these important crop plants.

Also of economic interest is to facilitate harvesting, which is madepossible by concentrating within a certain period of time thedehiscence, or reduction of adhesion to the tree, in citrus fruit,olives and other species and varieties of pomaceous fruit, stone fruitand nuts. The same mechanism, i.e. the promotion of the development ofabscission tissue between fruit part or leaf part and shoot part of theplants is also essential for the readily controllable defoliation ofuseful plants, in particular cotton.

Moreover, a shortening of the time interval in which the individualcotton plants mature leads to an increased fiber quality afterharvesting.

The compounds I, or the herbicidal compositions comprising the compoundsI, can be used, for example, in the form of ready-to-spray aqueoussolutions, powders, suspensions, also highly concentrated aqueous, oilyor other suspensions or dispersions, emulsions, oil dispersions, pastes,dusts, materials for broadcasting, or granules, by means of spraying,atomizing, dusting, spreading, watering or treatment of the seed ormixing with the seed. The use forms depend on the intended purpose; ineach case, they should ensure the finest possible distribution of theactive ingredients according to the invention.

The herbicidal compositions comprise a herbicidally effective amount ofat least one compound of the formula I or an agriculturally useful saltof I, and auxiliaries which are customary for the formulation of cropprotection agents.

Examples of auxiliaries customary for the formulation of crop protectionagents are inert auxiliaries, solid carriers, surfactants (such asdispersants, protective colloids, emulsifiers, wetting agents andtackifiers), organic and inorganic thickeners, bactericides, antifreezeagents, antifoams, if appropriate colorants and, for seed formulations,adhesives.

Examples of thickeners (i.e. compounds which impart to the formulationmodified flow properties, i.e. high viscosity in the state of rest andlow viscosity in motion) are polysaccharides, such as xanthan gum(Kelzan® from Kelco), Rhodopol® 23 (Rhone Poulenc) or Veegum® (from R.T.Vanderbilt), and also organic and inorganic sheet minerals, such asAttaclay® (from Engelhardt).

Examples of antifoams are silicone emulsions (such as, for example,Silikon® SRE, Wacker or Rhodorsil® from Rhodia), long-chain alcohols,fatty acids, salts of fatty acids, organofluorine compounds and mixturesthereof.

Bactericides can be added for stabilizing the aqueous herbicidalformulation. Examples of bactericides are bactericides based ondichlorophen and benzyl alcohol hemiformal (Proxel® from ICI orActicide® RS from Thor Chemie and Kathon® MK from Rohm & Haas), and alsoisothiazolinone derivates, such as alkylisothiazolinones andbenzisothiazolinones (Acticide MBS from Thor Chemie).

Examples of antifreeze agents are ethylene glycol, propylene glycol,urea or glycerol.

Examples of colorants are both sparingly water-soluble pigments andwater-soluble dyes. Examples which may be mentioned are the dyes knownunder the names Rhodamin B, C.I. Pigment Red 112 and C.I. Solvent Red 1,and also pigment blue 15:4, pigment blue 15:3, pigment blue 15:2,pigment blue 15:1, pigment blue 80, pigment yellow 1, pigment yellow 13,pigment red 112, pigment red 48:2, pigment red 48:1, pigment red 57:1,pigment red 53:1, pigment orange 43, pigment orange 34, pigment orange5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25,basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14,acid blue 9, acid yellow 23, basic red 10, basic red 108.

Examples of adhesives are polyvinylpyrrolidone, polyvinyl acetate,polyvinyl alcohol and tylose.

Suitable inert auxiliaries are, for example, the following:

mineral oil fractions of medium to high boiling point, such as keroseneand diesel oil, furthermore coal tar oils and oils of vegetable oranimal origin, aliphatic, cyclic and aromatic hydrocarbons, for exampleparaffin, tetrahydronaphthalene, alkylated naphthalenes and theirderivatives, alkylated benzenes and their derivatives, alcohols such asmethanol, ethanol, propanol, butanol and cyclohexanol, ketones such ascyclohexanone or strongly polar solvents, for example amines such asN-methylpyrrolidone, and water.

Solid carriers are mineral earths such as silicas, silica gels,silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay,dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate andmagnesium oxide, ground synthetic materials, fertilizers such asammonium sulfate, ammonium phosphate, ammonium nitrate and ureas, andproducts of vegetable origin, such as cereal meal, tree bark meal, woodmeal and nutshell meal, cellulose powders, or other solid carriers.

Suitable surfactants (adjuvants, wetting agents, tackifiers, dispersantsand also emulsifiers) are the alkali metal salts, alkaline earth metalsalts and ammonium salts of aromatic sulfonic acids, for examplelignosulfonic acids (e.g. Borrespers-types, Borregaard), phenolsulfonicacids, naphthalenesulfonic acids (Morwet types, Akzo Nobel) anddibutylnaphthalenesulfonic acid (Nekal types, BASF SE), and of fattyacids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ethersulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta-and octadecanols, and also of fatty alcohol glycol ethers, condensatesof sulfonated naphthalene and its derivatives with formaldehyde,condensates of naphthalene or of the naphthalenesulfonic acids withphenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylatedisooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenylpolyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol,fatty alcohol/ethylene oxide condensates, ethoxylated castor oil,polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, laurylalcohol polyglycol ether acetate, sorbitol esters, lignosulfite wasteliquors and proteins, denatured proteins, polysaccharides (e.g.methylcellulose), hydrophobically modified starches, polyvinyl alcohol(Mowiol types Clariant), polycarboxylates (BASF SE, Sokalan types),polyalkoxylates, polyvinylamine (BASF SE, Lupamine types),polyethyleneimine (BASF SE, Lupasol types), polyvinylpyrrolidone andcopolymers thereof.

Powders, materials for broadcasting and dusts can be prepared by mixingor grinding the active ingredients together with a solid carrier.

Granules, for example coated granules, impregnated granules andhomogeneous granules, can be prepared by binding the active ingredientsto solid carriers.

Aqueous use forms can be prepared from emulsion concentrates,suspensions, pastes, wettable powders or water-dispersible granules byadding water. To prepare emulsions, pastes or oil dispersions, thecompounds of the formula I or Ia, either as such or dissolved in an oilor solvent, can be homogenized in water by means of a wetting agent,tackifier, dispersant or emulsifier. Alternatively, it is also possibleto prepare concentrates comprising active substance, wetting agent,tackifier, dispersant or emulsifier and, if desired, solvent or oil,which are suitable for dilution with water.

The concentrations of the compounds of the formula I in the ready-to-usepreparations can be varied within wide ranges. In general, theformulations comprise from 0.001 to 98% by weight, preferably 0.01 to95% by weight of at least one active compound. The active compounds areemployed in a purity of from 90% to 100%, preferably 95% to 100%(according to NMR spectrum).

The compounds I of the invention can for example be formulated asfollows:

1. Products for Dilution with Water

A Water-Soluble Concentrates

10 parts by weight of active compound are dissolved in 90 parts byweight of water or a water-soluble solvent. As an alternative, wettersor other adjuvants are added. The active compound dissolves upondilution with water. This gives a formulation with an active compoundcontent of 10% by weight.

B Dispersible Concentrates

20 parts by weight of active compound are dissolved in 70 parts byweight of cyclohexanone with addition of 10 parts by weight of adispersant, for example polyvinylpyrrolidone. Dilution with water givesa dispersion. The active compound content is 20% by weight.

C Emulsifiable Concentrates

15 parts by weight of active compound are dissolved in 75 parts byweight of an organic solvent (e.g. alkylaromatics) with addition ofcalcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case5 parts by weight). Dilution with water gives an emulsion. Theformulation has an active compound content of 15% by weight.

D Emulsions

25 parts by weight of active compound are dissolved in 35 parts byweight of an organic solvent (e.g. alkylaromatics) with addition ofcalcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case5 parts by weight). This mixture is introduced into 30 parts by weightof water by means of an emulsifier (e.g. Ultraturrax) and made into ahomogeneous emulsion. Dilution with water gives an emulsion. Theformulation has an active compound content of 25% by weight.

E Suspensions

In an agitated ball mill, 20 parts by weight of active compound arecomminuted with addition of 10 parts by weight of dispersants andwetters and 70 parts by weight of water or an organic solvent to give afine active compound suspension. Dilution with water gives a stablesuspension of the active compound. The active compound content in theformulation is 20% by weight.

F Water-Dispersible Granules and Water-Soluble Granules

50 parts by weight of active compound are ground finely with addition of50 parts by weight of dispersants and wetters and made intowater-dispersible or water-soluble granules by means of technicalappliances (for example extrusion, spray tower, fluidized bed). Dilutionwith water gives a stable dispersion or solution of the active compound.The formulation has an active compound content of 50% by weight.

G Water-Dispersible Powders and Water-Soluble Powders

75 parts by weight of active compound are ground in a rotor-stator millwith addition of 25 parts by weight of dispersants, wetters and silicagel. Dilution with water gives a stable dispersion or solution of theactive compound. The active compound content of the formulation is 75%by weight.

H Gel Formulations

In a ball mill, 20 parts by weight of active compound, 10 parts byweight of dispersant, 1 part by weight of gelling agent and 70 parts byweight of water or of an organic solvent are ground to give a finesuspension. Dilution with water gives a stable suspension with activecompound content of 20% by weight.

2. Products to be Applied Undiluted

I Dusts

5 parts by weight of active compound are ground finely and mixedintimately with 95 parts by weight of finely divided kaolin. This givesa dusting powder with an active compound content of 5% by weight.

J Granules (GR, FG, GG, MG)

0.5 parts by weight of active compound are ground finely and associatedwith 99.5 parts by weight of carriers. Current methods here areextrusion, spray-drying or the fluidized bed. This gives granules to beapplied undiluted with an active compound content of 0.5% by weight.

K ULV Solutions (UL)

10 parts by weight of active compound are dissolved in 90 parts byweight of an organic solvent, for example xylene. This gives a productto be applied undiluted with an active compound content of 10% byweight.

The compounds I or the herbicidal compositions comprising them can beapplied pre- or post-emergence, or together with the seed of a cropplant. It is also possible to apply the herbicidal compositions oractive compounds by applying seed, pretreated with the herbicidalcompositions or active compounds, of a crop plant. If the activecompounds are less well tolerated by certain crop plants, applicationtechniques may be used in which the herbicidal compositions are sprayed,with the aid of the spraying equipment, in such a way that as far aspossible they do not come into contact with the leaves of the sensitivecrop plants, while the active compounds reach the leaves of undesirableplants growing underneath, or the bare soil surface (post-directed,lay-by).

In a further embodiment, the compounds of the formula I or theherbicidal compositions can be applied by treating seed.

The treatment of seed comprises essentially all procedures familiar tothe person skilled in the art (seed dressing, seed coating, seeddusting, seed soaking, seed film coating, seed multilayer coating, seedencrusting, seed dripping and seed pelleting) based on the compounds ofthe formula I according to the invention or the compositions preparedtherefrom. Here, the herbicidal compositions can be applied diluted orundiluted.

The term seed comprises seed of all types, such as, for example, corns,seeds, fruits, tubers, cuttings and similar forms. Here, preferably, theterm seed describes corns and seeds.

The seed used can be seed of the useful plants mentioned above, but alsothe seed of transgenic plants or plants obtained by customary breedingmethods.

The rates of application of active compound are from 0.001 to 3.0,preferably 0.01 to 1.0, kg/ha of active substance (a.s.), depending onthe control target, the season, the target plants and the growth stage.To treat the seed, the compounds I are generally employed in amounts offrom 0.001 to 10 kg per 100 kg of seed.

It may also be advantageous to use the compounds of the formula I incombination with safeners. Safeners are chemical compounds which preventor reduce damage to useful plants without substantially affecting theherbicidal action of the compounds of the formula I on unwanted plants.They can be used both before sowing (for example in the treatment ofseed, or on cuttings or seedlings) and before or after the emergence ofthe useful plant. The safeners and the compounds of the formula I can beused simultaneously or in succession. Suitable safeners are, forexample, (quinolin-8-oxy)acetic acids,1-phenyl-5-haloalkyl-1H-1,2,4-triazole-3-carboxylic acids,1-phenyl-4,5-dihydro-5-alkyl-1H-pyrazole-3,5-dicarboxylic acids,4,5-dihydro-5,5-diaryl-3-isoxazolecarboxylic acids, dichloroacetamides,alpha-oximinophenylacetonitriles, acetophenone oximes,4,6-dihalo-2-phenylpyrimidines,N-[[4-(aminocarbonyl)phenyl]-sulfonyl]-2-benzamides, 1,8-naphthalicanhydride, 2-halo-4-(haloalkyl)-5-thiazolecarboxylic acids,phosphorothiolates and O-phenyl N-alkylcarbamates and theiragriculturally useful salts and, provided that they have an acidfunction, their agriculturally useful derivatives, such as amides,esters and thioesters.

To broaden the activity spectrum and to obtain synergistic effects, thecompounds of the formula I can be mixed and jointly applied withnumerous representatives of other herbicidal or growth-regulating groupsof active compounds or with safeners. Suitable mixing partners are, forexample, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoricacid and its derivatives, aminotriazoles, anilides,aryloxy/heteroaryloxyalkanoic acids and their derivatives, benzoic acidand its derivatives, benzothiadiazinones,2-(hetaroyl/aroyl)-1,3-cyclohexanediones, heteroaryl aryl ketones,benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates,quinoline carboxylic acid and its derivatives, chloroacetanilides,cyclohexenone oxime ether derivates, diazines, dichloropropionic acidand its derivatives, dihydrobenzofurans, dihydrofuran-3-ones,dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls,halocarboxylic acids and their derivatives, ureas, 3-phenyluracils,imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides,oxadiazoles, oxiranes, phenols, aryloxy- andheteroaryloxyphenoxypropionic esters, phenylacetic acid and itsderivatives, 2-phenylpropionic acid and its derivatives, pyrazoles,phenylpyrazoles, pyridazines, pyridinecarboxylic acid and itsderivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines,triazinones, triazolinones, triazolecarboxamides, uracils and alsophenylpyrazolines and isoxazolines and their derivatives.

Moreover, it may be useful to apply the compounds I alone or incombination with other herbicides or else also mixed with further cropprotection agents, jointly, for example with compositions forcontrolling pests or phytopathogenic fungi or bacteria. Also of interestis the miscibility with mineral salt solutions which are employed foralleviating nutritional and trace element deficiencies. Other additivessuch as nonphytotoxic oils and oil concentrates may also be added.

Examples of herbicides which can be used in combination with thepyridine compounds of the formula I according to the present inventionare:

b1) from the group of the lipid biosynthesis inhibitors:

alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop,clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop,diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P,fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P,fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P,haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop,quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P,quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim,tralkoxydim, benfuresate, butylate, cycloate, dalapon, dimepiperate,EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb,pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate andvernolate;

b2) from the group of the ALS inhibitors:

amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl,bispyribac, bispyribac-sodium, chlorimuron, chlorimuron-ethyl,chlorsulfuron, cinosulfuron, cloransulam, cloransulam-methyl,cyclosulfamuron, diclosulam, ethametsulfuron, ethametsulfuron-methyl,ethoxysulfuron, flazasulfuron, florasulam, flucarbazone,flucarbazone-sodium, flucetosulfuron, flumetsulam, flupyrsulfuron,flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron,halosulfuron-methyl, imazamethabenz, imazamethabenz-methyl, imazamox,imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron,iodosulfuron-methyl-sodium, mesosulfuron, metosulam, metsulfuron,metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron,penoxsulam, primisulfuron, primisulfuron-methyl, propoxycarbazone,propoxycarbazone-sodium, prosulfuron, pyrazosulfuron,pyrazosulfuron-ethyl, pyribenzoxim, pyrimisulfan, pyriftalid,pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium,pyroxsulam, rimsulfuron, sulfometuron, sulfometuron-methyl,sulfosulfuron, thiencarbazone, thiencarbazone-methyl, thifensulfuron,thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl,trifloxysulfuron, triflusulfuron, triflusulfuron-methyl andtritosulfuron;

b3) from the group of the photosynthesis inhibitors:

ametryn, amicarbazone, atrazine, bentazone, bentazone-sodium, bromacil,bromofenoxim, bromoxynil and its salts and esters, chlorobromuron,chloridazone, chlorotoluron, chloroxuron, cyanazine, desmedipham,desmetryn, dimefuron, dimethametryn, diquat, diquat-dibromide, diuron,fluometuron, hexazinone, ioxynil and its salts and esters, isoproturon,isouron, karbutilate, lenacil, linuron, metamitron, methabenzthiazuron,metobenzuron, metoxuron, metribuzin, monolinuron, neburon, paraquat,paraquat-dichloride, paraquat-dimetilsulfate, pentanochlor,phenmedipham, phenmedipham-ethyl, prometon, prometryn, propanil,propazine, pyridafol, pyridate, siduron, simazine, simetryn,tebuthiuron, terbacil, terbumeton, terbuthylazine, terbutryn,thidiazuron and trietazine;

b4) from the group of the protoporphyrinogen-IX oxidase inhibitors:

acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone,benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl,chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl,flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen,fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen,halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone,profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil,sulfentrazone, thidiazimin,2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-N-[(isopropyl)-methylsulfamoyl]benzamide(H-1; CAS 372137-35-4),ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate(H-2; CAS 353292-31-6),N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(H-3; CAS 452098-92-9),N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(H-4; CAS 915396-43-9),N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(H-5; CAS 452099-05-7) andN-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(H-6; CAS 45100-03-7);

b5) from the group of the bleacher herbicides:

aclonifen, amitrol, beflubutamid, benzobicyclon, benzolenap, clomazone,diflufenican, fluridone, fluorochloridone, flurtamone, isoxaflutole,mesotrione, norflurazon, picolinafen, pyrasulfutole, pyrazolynate,pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, topramezone,4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridyl]carbonyl]bicyclo[3.2.1]oct-3-en-2-one(H-7; CAS 352010-68-5) and4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (H-8;CAS 180608-33-7);

b6) from the group of the EPSP synthase inhibitors:

glyphosate, glyphosate-isopropylammonium and glyphosate-trimesium(sulfosate);

b7) from the group of the glutamine synthase inhibitors:

bilanaphos (bialaphos), bilanaphos-sodium, glufosinate andglufosinate-ammonium;

b8) from the group of the DHP synthase inhibitors:

asulam;

b9) from the group of the mitose inhibitors:

amiprophos, amiprophos-methyl, benfluralin, butamiphos, butralin,carbetamide, chlorpropham, chlorthal, chlorthal-dimethyl, dinitramine,dithiopyr, ethalfluralin, fluchloralin, oryzalin, pendimethalin,prodiamine, propham, propyzamide, tebutam, thiazopyr and trifluralin;

b10) from the group of the VLCFA inhibitors:

acetochlor, alachlor, anilofos, butachlor, cafenstrole, dimethachlor,dimethanamid, dimethenamid-P, diphenamid, fentrazamide, flufenacet,mefenacet, metazachlor, metolachlor, metolachlor-S, naproanilide,napropamide, pethoxamid, piperophos, pretilachlor, propachlor,propisochlor, pyroxasulfone (KIH-485) and thenylchlor;

Compounds of the formula 2:

in which the variables have the following meanings:Y is phenyl or 5- or 6-membered heteroaryl as defined at the outset,which radicals may be substituted by one to three groups R^(aa); R²¹,R²², R²³, R²⁴ are H, halogen or C₁-C₄-alkyl; X is O or NH; N is 0 or 1.

Compounds of the formula 2 have in particular the following meanings:

Y is

where # denotes the bond to the skeleton of the molecule; andR²¹, R²², R²³, R²⁴ are H, Cl, F or CH₃; R²⁵ is halogen, C₁-C₄-alkyl orC₁-C₄-haloalkyl; R²⁶ is C₁-C₄-alkyl; R²⁷ is halogen, C₁-C₄-alkoxy orC₁-C₄-haloalkoxy; R²⁸ is H, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl orC₁-C₄-haloalkoxy; M is 0, 1, 2 or 3; X is oxygen; N is 0 or 1.

Preferred compounds of the formula 2 have the following meanings:

Y

R²¹ is H; R²², R²³ are F; R²⁴ is H or F; X is oxygen; N is 0 or 1.

Particularly preferred compounds of the formula 2 are:3-[5-(2,2-difluoroethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethanesulfonyl]-4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole(2-1);3-{[5-(2,2-difluoroethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl]fluoromethanesulfonyl}-5,5-dimethyl-4,5-dihydroisoxazole(2-2);4-(4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonylmethyl)-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole(2-3);4-[(5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl)fluoromethyl]-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole(2-4);4-(5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonylmethyl)-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole(2-5);3-{[5-(2,2-difluoroethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl]difluoromethanesulfonyl}-5,5-dimethyl-4,5-dihydroisoxazole(2-6);4-[(5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl)difluoromethyl]-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole(2-7);3-{[5-(2,2-difluoroethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl]difluoromethanesulfonyl}-4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole(2-8);4-[difluoro-(4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl)methyl]-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole(2-9);

b11) from the group of the cellulose biosynthesis inhibitors:

chlorthiamid, dichlobenil, flupoxam and isoxaben;

b12) from the group of the decoupler herbicides:

dinoseb, dinoterb and DNOC and its salts;

b13) from the group of the auxin herbicides:

2,4-D and its salts and esters, 2,4-DB and its salts and esters,aminopyralid and its salts such asaminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin,benazolin-ethyl, chloramben and its salts and esters, clomeprop,clopyralid and its salts and esters, dicamba and its salts and esters,dichlorpropand its salts and esters, dichlorprop-P and its salts andesters, fluoroxypyr, fluoroxypyr-butomethyl, fluoroxypyr-meptyl, MCPAand its salts and esters, MCPA-thioethyl, MCPB and its salts and esters,mecopropand its salts and esters, mecoprop-P and its salts and esters,picloram and its salts and esters, quinclorac, quinmerac, TBA (2,3,6)and its salts and esters, triclopyr and its salts and esters, and5,6-dichloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (H-9; CAS858956-08-8) and its salts and esters;

b14) from the group of the auxin transport inhibitors: diflufenzopyr,diflufenzopyr-sodium, naptalam and naptalam-sodium;

b15) from the group of the other herbicides: bromobutide, chlorflurenol,chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet,difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron,endothal and its salts, etobenzanid, flamprop, flamprop-isopropyl,flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol,flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan,maleic hydrazide, mefluidide, metam, methyl azide, methyl bromide,methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone,pelargonic acid, pyributicarb, quinoclamine, triaziflam, tridiphane and6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (H-10; CAS499223-49-3) and its salts and esters.

Examples of preferred safeners C are benoxacor, cloquintocet,cyometrinil, cyprosulfamide, dichlormid, dicyclonone, dietholate,fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen,mefenpyr, mephenate, naphthalic anhydride, oxabetrinil,4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (H-11; MON4660, CAS71526-07-3) and 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine(H-12; R-29148, CAS 52836-31-4).

The active compounds of groups b1) to b15) and the safeners C are knownherbicides and safeners, see, for example, The Compendium of PesticideCommon Names (http://www.alanwood.net/pesticides/); B. Hock, C. Fedtke,R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart,1995. Further herbicidally active compounds are known from WO 96/26202,WO 97/41116, WO 97/41117, WO 97/41118, WO 01/83459 and WO 2008/074991and from W. Kramer et al. (ed.) “Modern Crop Protection Compounds”, Vol.1, Wiley VCH, 2007 and the literature quoted therein.

The invention also relates to compositions in the form of a cropprotection composition formulated as a 1-component compositioncomprising an active compound combination comprising at least onepyridine compound of the formula I and at least one further activecompound, preferably selected from the active compounds of groups b1 tob15, and at least one solid or liquid carrier and/or one or moresurfactants and, if desired, one or more further auxiliaries customaryfor crop protection compositions.

The invention also relates to compositions in the form of a cropprotection composition formulated as a 2-component compositioncomprising a first component comprising at least one pyridine compoundof the formula I, a solid or liquid carrier and/or one or moresurfactants and a second component comprising at least one furtheractive compound selected from the active compounds of groups b1 to b15,a solid or liquid carrier and/or one or more surfactants, whereadditionally both components may also comprise further auxiliariescustomary for crop protection compositions.

In binary compositions comprising at least one compound of the formula Ias component A and at least one herbicide B, the weight ratio of theactive compounds A:B is generally in the range of from 1:1000 to 1000:1,preferably in the range of from 1:500 to 500:1, in particular in therange of from 1:250 to 250:1 and particularly preferably in the range offrom 1:75 to 75:1.

In binary compositions comprising at least one compound of the formula Ias component A and at least one safener C, the weight ratio of theactive compounds A:C is generally in the range of from 1:1000 to 1000:1,preferably in the range of from 1:500 to 500:1, in particular in therange of from 1:250 to 250:1 and particularly preferably in the range offrom 1:75 to 75:1.

In ternary compositions comprising both at least one compound of theformula I as component A, at least one herbicide B and at least onesafener C, the relative parts by weight of the components A:B aregenerally in the range of from 1:1000 to 1000:1, preferably in the rangeof from 1:500 to 500:1, in particular in the range of from 1:250 to250:1 and particularly preferably in the range of from 1:75 to 75:1; theweight ratio of the components A:C is generally in the range of from1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, inparticular in the range of from 1:250 to 250:1 and particularlypreferably in the range of from 1:75 to 75:1; and the weight ratio ofthe components B:C is generally in the range of from 1:1000 to 1000:1,preferably in the range of from 1:500 to 500:1, in particular in therange of from 1:250 to 250:1 and particularly preferably in the range offrom 1:75 to 75:1. Preferably, the weight ratio of the components A+B tothe component C is in the range of from 1:500 to 500:1, in particular inthe range of from 1:250 to 250:1 and particularly preferably in therange of from 1:75 to 75:1.

The active compounds in the compositions described are in each casepreferably present in synergistically effective amounts.

The compounds I and the compositions according to the invention may alsohave a plant-strengthening action. Accordingly, they are suitable formobilizing the defense system of the plants against attack by unwantedmicroorganisms, such as harmful fungi, but also viruses and bacteria.Plant-strengthening (resistance-inducing) substances are to beunderstood as meaning, in the present context, those substances whichare capable of stimulating the defense system of treated plants in sucha way that, when subsequently inoculated by unwanted microorganisms, thetreated plants display a substantial degree of resistance to thesemicroorganisms.

The compounds I can be employed for protecting plants against attack byunwanted microorganisms within a certain period of time after thetreatment. The period of time within which their protection is effectedgenerally extends from 1 to 28 days, preferably from 1 to 14 days, afterthe treatment of the plants with the compounds I, or, after treatment ofthe seed, for up to 9 months after sowing.

The compounds I and the compositions according to the invention are alsosuitable for increasing the harvest yield.

Moreover, they have reduced toxicity and are tolerated well by theplants.

Hereinbelow, the preparation of quinolinone compounds of the formula Iis illustrated by way of examples, without limiting the subject matterof the present invention to the examples shown.

PREPARATION EXAMPLES Preparation of 6,8-Dihydroxy-7-o-tolylquinolineStep 1: 2-Iodo-1,3-dimethoxy-4-nitrobenzene

1,3-Difluoro-2-iodo-4-nitrobenzene (5.0 g, 17.5 mmol) was dissolved in50 ml of methanol, and NaOMe (3.79 g, 70.1 mmol) was added. The solutionwas heated under reflux for 16 h. After concentration, the residue waschromatographed on silica gel using petroleum ether/ethyl acetate. Thisgave 2-iodo-1,3-dimethoxy-4-nitrobenzene (3 g) as a yellowish powder.

¹H-NMR (400 MHz, CDCl₃): 8.0 (d, 1H); 6.88 (d, 1H); 3.96 (s, 3H); 3.91(s, 3H)

Step 2: 2,6-Dimethoxy-2′-methyl-3-nitrobiphenyl

2-Iodo-1,3-dimethoxy-4-nitrobenzene (0.5 g, 1.62 mmol) was dissolved indioxane/acetonitrile/water (10 ml/2 ml/2 ml), and 2-tolylboronic acidwas added. Pd(dppf)Cl₂ (0.11 mg, 0.16 mmol) and K₂CO₃ (0.33 g, 2.43mmol) were added to this, and the mixture was stirred at 90° C. for 32h. After concentration, the residue was chromatographed on silica gelusing petroleum ether/ethyl acetate. This gave2,6-dimethoxy-2′-methyl-3-nitrobiphenyl (0.2 g) as a colorless powder.

¹H-NMR (400 MHz, CDCl₃): 7.99 (d, 1H); 7.15-7.35 (m, 4H); 6.79 (d, 1H);3.82 (s, 3H); 3.45 (s, 3H); 2.10 (s, 3H)

Step 3: 2,6-Dimethoxy-2′-methylbiphenyl-3-ylamine

Pd/C (0.1 g) was added to 2,6-dimethoxy-2′-methyl-3-nitrobiphenyl (0.2g, 0.73 mmol) in methanol (20 ml), and under 1 atm of H₂, the mixturewas heated at 50° C. for 2 h. Filtration and concentration gave2,6-dimethoxy-2′-methylbiphenyl-3-ylamine (0.14 g) as a colorless oil,which was directly reacted further.

Step 4: 6,8-Dimethoxy-7-o-tolylquinoline

6-Dimethoxy-2′-methylbiphenyl-3-ylamine (0.14 g, 0.58 mmol), acrolein(100 mg, 1.8 mmol) and 1N HCl (4 ml) were heated at 90° C. for 2 h.After cooling, the mixture was diluted with ethyl acetate (10 ml) andneutralized with saturated NaHCO₃ solution, the aqueous phase wasextracted 2× with ethyl acetate (3 ml) and the organic phase was driedwith Na₂SO₄ and concentrated. The residue was chromatographed on silicagel using petroleum ether/ethyl acetate. This gave6,8-dimethoxy-7-o-tolylquinoline (80 mg) as yellowish crystals.

¹H-NMR (400 MHz, CDCl₃): 8.83 (m, 1H); 8.10 (d, 1H); 7.2-7.4 (m, 5H);6.95 (s, 1H); 3.85 (s, 3H); 3.77 (s, 3H); 2.13 (s, 3H)

Step 5: 6,8-Dihydroxy-7-o-tolylquinoline

At −78° C., 1N BBr₃ in CH₂Cl₂ (1.5 ml, 1.5 mmol) was added to6,8-dimethoxy-7-o-tolylquinoline (0.10 g, 0.36 mmol) in CH₂Cl₂ (5 ml),and the mixture was warmed to room temperature and stirred for 6 h. Thesolution was poured into ice-water and neutralized with saturated NaHCO₃solution. The mixture was extracted with ethyl acetate, and the organicphase was dried with Na₂SO₄. Purification of the residue by HPLC gave6,8-dihydroxy-7-o-tolylquinoline (7 mg) as a white powder.

¹H-NMR (400 MHz, CDCl₃): 8.63 (d, 1H); 8.05 (d, 1H); 7.30-7.45 (m, 5H);6.89 (s, 1H); 2.21 (s, 3H)

MS (M+H): 251.9

Use Examples

The herbicidal activity of the compound of the formula I is demonstratedby the following greenhouse experiments:

The culture containers used are plastic flowerpots containing loamy sandwith approximately 3.0% of humus as the substrate. The seeds of the testplants are sown separately for each species.

For the pre-emergence treatment, the active ingredients, which have beensuspended or emulsified in water, are applied directly after sowing bymeans of finely distributing nozzles. The containers are irrigatedgently to promote germination and growth and subsequently covered withtransparent plastic hoods until the plants have rooted. This covercauses uniform germination of the test plants, unless this has beenimpaired by the active ingredients.

For the post-emergence treatment, the test plants are first grown to aheight of 3 to 15 cm, depending on the plant habit, and only thentreated with the active ingredients which has been suspended oremulsified in water. For this purpose, the test plants are either sowndirectly and grown in the same containers, or they are first grownseparately as seedlings and transplanted into the test containers a fewdays prior to treatment.

Depending on the species, the plants are kept at 10 to 25° C. or 20 to35° C. The test period extends over 2 to 4 weeks. During this time, theplants are tended, and their response to the individual treatments isevaluated.

Evaluation is carried out using a scale from 0 to 100. 100 means noemergence of the plants, or complete destruction of at least the aerialmoieties, and 0 means no damage, or normal course of growth. A goodherbicidal activity is given at values of at least 70 and a very goodherbicidal activity is given at values of at least 85.

1. A quinolinone compound of the formula I

in which R¹ is O—R^(A), S(O), —R^(A) or O—S(O), —R^(A); R^(A) is hydrogen, C₁-C₄-alkyl, Z—C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl, C₂-C₆-alkenyl, Z—C₃-C₆-cycloalkenyl, C₂-C₆-alkynyl, Z-(tri-C₁-C₄-alkyl)silyl, Z—C(═O)—R^(a), Z—P(═O)(R^(a))₂, NR^(i)R^(ii), a 3- to 7-membered monocyclic or 9- or 10-membered bicyclic saturated, unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, which may be partially or fully substituted by groups R^(a) and/or R^(b) and which is attached via carbon or nitrogen, R^(a) is hydrogen, OH, C₁-C₈-alkyl, C₁-C₄-haloalkyl, Z—C₃-C₆-cycloalkyl, C₂-C₈-alkenyl, Z—C₅-C₆-cycloalkenyl, C₂-C₈-alkynyl, Z—C₁-C₆-alkoxy, Z—C₁-C₄-haloalkoxy, Z—C₃-C₈-alkenyloxy, Z—C₃-C₈-alkynyloxy, NR^(i)R^(ii), C₁-C₆-alkylsulfonyl, Z-(tri-C₁-C₄-alkyl)silyl, Z-phenyl, Z-phenoxy, Z-phenylamino or a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where the cyclic groups are unsubstituted or substituted by 1, 2, 3 or 4 groups R^(b); R^(i), R^(ii) independently of one another are hydrogen, C₁-C₈-alkyl, C₁-C₄-haloalkyl, C₃-C₈-alkenyl, C₃-C₈-alkynyl, Z—C₃-C₆-cycloalkyl, Z—C₁-C₈-alkoxy, Z—C₁-C₈-haloalkoxy, Z—C(═O)—R^(a), Z-phenyl, a 3- to 7-membered monocyclic or 9- or 10-membered bicyclic saturated, unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S and which is attached via Z; or R^(i) and R^(ii) together with the nitrogen atom to which they are attached may also form a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S; Z is a covalent bond or C₁-C₄-alkylene; n is 0, 1 or 2; R² is phenyl, naphthyl or a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where the cyclic groups are unsubstituted or substituted by 1, 2, 3 or 4 groups R^(b); R^(b) independently of one another are Z—CN, Z—OH, Z—NO₂, Z-halogen, C₁-C₈-alkyl, C₁-C₄-haloalkyl, C₂-C₈-alkenyl, C₂-C₈-alkynyl, Z—C₁-C₈-alkoxy, Z—C₁-C₈-haloalkoxy, Z—C₃-C₁₀-cycloalkyl, O—Z—C₃-C₁₀-cycloalkyl, Z—C(═O)—R^(a), NR^(i)R^(ii), Z-(tri-C₁-C₄-alkyl)silyl, Z-phenyl and S(O)_(n)R^(bb), where R^(bb) is C₁-C₈-alkyl or C₁-C₆-haloalkyl and n is 0, 1 or 2; R^(b) together with the group R^(b) attached to the adjacent carbon atom may also form a five- or six-membered saturated or partially or fully unsaturated ring which, in addition to carbon atoms, may contain 1, 2 or 3 heteroatoms selected from the group consisting of O, N and S; X is O, S or N—R⁵; R³, R⁴, R⁵ independently of one another are hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₃-C₆-alkynyl, Z—C₃-C₁₀-cycloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-cyanoalkyl, Z-phenyl, Z—C(═O)—R^(a)2 or tri-C₁-C₄-alkylsilyl; R^(a)2 is C₁-C₆-alkyl, C₁-C₄-haloalkyl, Z—C₁-C₆-alkoxy, Z—C₁-C₄-haloalkoxy or NR^(i)R^(ii); one of A, E, G, and M is N and the other three are C—R^(c); R^(c) is hydrogen or one of the groups mentioned for R^(b); where in the groups R^(A), R³, R⁴ and R⁵ and their substituents, the carbon chains and/or the cyclic groups may be partially or fully substituted by groups R^(b), or a N-oxide or an agriculturally suitable salt thereof.
 2. The compound of the formula I according to claim 1 in which X is O.
 3. The compound of the formula I according to claim 1 in which X is S.
 4. The compound of the formula I according to claim 1 in which X is N—R⁵.
 5. The compound of the formula I according to claim 1 in which R¹ is O—R^(A) or O—S(O)_(n)—R^(A).
 6. The compound of the formula I according to claim 1 which corresponds to the formula I.1

in which R^(c1), R^(c2) and R^(c3) each correspond to a group R^(c).
 7. The compound of the formula I according to claim 1 which corresponds to the formula I.2

in which R^(c1), R^(c2) and R^(c4) each correspond to a group R^(c).
 8. The compound of the formula I according to claim 1 which corresponds to the formula I.A

in which R⁶ and R⁷ are groups R^(b) and m is zero or an integer from one to four.
 9. A composition comprising a herbicidally effective amount of at least one quinolinone of the formula I or an agriculturally suitable salt thereof according to claim 1 and auxiliaries customary for formulating crop protection agents.
 10. The composition according to claim 9 which comprises at least one further active compound.
 11. The composition according to claim 9 which comprises two further active compounds from the group of the herbicides and/or safeners.
 12. A method for controlling unwanted vegetation which comprises allowing a herbicidally effective amount of at least one quinolinone of the formula I or of an agriculturally suitable salt thereof according to claim 1 to act on plants, their seed and/or their habitat.
 13. The method of claim 12, wherein X is O.
 14. The method of claim 12, wherein X is S.
 15. The method of claim 12, wherein X is N—R⁵.
 16. The method of claim 12, wherein R¹ is O—R^(A) or O—S(O)_(n)—R^(A).
 17. The method of claim 12, wherein the compound of formula I is I.1

in which R^(c1), R^(c2) and R^(c3) each correspond to a group R^(c).
 18. The method of claim 12, wherein the compound of formula I is I.2

in which R^(c1), R^(c2) and R^(c4) each correspond to a group R^(c).
 19. The method of claim 12, wherein the compound of formula I is I.A

in which R⁶ and R⁷ are groups R^(b) and m is zero or an integer from one to four. 